- Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization
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The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.
- Korch, Katerina M.,Watson, Donald A.
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supporting information
p. 7285 - 7289
(2021/09/14)
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- Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C?H Functionalization
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High-valent cyclopentadienyl cobalt catalysis is a versatile tool for sustainable C?H bond functionalizations. To harness the full potential of this strategy, control of the stereoselectivity of these processes is necessary. Herein, we report highly enant
- Ozols, Kristers,Onodera, Shunsuke,Wo?niak, ?ukasz,Cramer, Nicolai
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supporting information
p. 655 - 659
(2020/12/01)
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- Synthesis of ortho-phenolic sulfilimines via an intermolecular sulfur atom transfer cascade reaction
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To expand the toolbox for the synthesis of ortho-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction has a wide substrate scope and can be conducted on a gram scale with excellent reaction efficiency.
- Ren, Yan,Song, Yinan,Xiong, Feng,Xu, Shaojian,Zhang, Linxing,Zhang, Xinhao,Zuo, Yingying
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supporting information
p. 3799 - 3803
(2020/06/08)
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- Fe3O4@SiO2-copper sucrose xanthate as a green nanocatalyst for N-, O- and S-arylation
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Formation of C(sp2)–X bonds was carried out using a Fe3O4@SiO2-copper(I) sucrose xanthate nanoparticle catalyst with the aid of the copper(I) xanthate moiety in the catalyst which was prepared from the reaction between sucrose and carbon disulfide through an alkaline medium via the traditional Zeise approach. Various techniques were employed for the characterization of these novel nanoparticles. Three sorts of heteroatoms, N, O and S, successfully underwent heteroatom arylation to produce secondary or tertiary amines, ethers and thioethers, respectively.
- Radfar, Iman,Kazemi Miraki, Maryam,Esfandiary, Naghmeh,Ghandi, Leila,Heydari, Akbar
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- Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of N-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C-H/C-C Activations
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A cascade [3 + 2] annulation and ring opening of N-aryloxyacetamides with 1-alkynylcyclobutanols via Rh(III)-catalyzed redox-neutral C-H/C-C activations using internal oxidative O-NHAc and -OH as the dual directing groups has been achieved. This reaction provided an efficient and regioselective approach to benzofuran derivatives with good functional group compatibility and high yields.
- Pan, Jin-Long,Liu, Chang,Chen, Chao,Liu, Tuan-Qing,Wang, Man,Sun, Zhenliang,Zhang, Shu-Yu
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supporting information
p. 2823 - 2827
(2019/04/30)
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- An internal oxidant-directing strategy enabling transition metal-free C–S bond ligation
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Organic sulfur compounds have broad applications in biology, medicine and material sciences and intensive efforts have been devoted to developing mild and general C–S bond-forming methods. However, a mild, transition-metal-free, direct C–H bond functionalization method remains elusive. Here, we report the use of an internal oxidant-directing strategy to achieve this goal. The cascade reactions described here show excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. This study enlarges the synthesis toolbox for preparing structurally diverse sulfilimines under mild conditions.
- Zuo, Yingying,Xiong, Feng,Zhao, Jing
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supporting information
p. 4174 - 4179
(2019/05/24)
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- RhIII-Catalyzed Decarboxylative o-Acylation of Arenes Bearing an Oxidizing Directing Group
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Here in we report, rhodium(III)-catalyzed decarboxylative acylation of arenes using α-oxocarboxylic acids as acyl surrogate. In this strategy, O–NHAc group act as an autocleavable oxidizing directing group (ODGauto), thus giving rise to ortho-acylated phenols in moderate to good yields. Mechanistic studies provided strong support for a kinetically relevant C–H bond activation. According to the best of our knowledge, this is the first report of Rhodium catalyzed decarboxylative acylation.
- Bera, Suvankar,Chandrasekhar,Chatterjee, Satadru,Killi, Sunil Kumar,Sarkar, Debabrata,Banerji, Biswadip
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supporting information
p. 3877 - 3881
(2019/06/28)
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- Synthesis of Benzofurans and Benzoxazoles through a [3,3]-Sigmatropic Rearrangement: O-NHAc as a Multitasking Functional Group
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The synthesis of heterocycles relies heavily on diverse sigmatropic rearrangements triggered by the cleavage of X-Y (X, Y = C, O, N, S, I) bonds. However, a unified rearrangement approach for constructing heterocyclic libraries is highly desirable. Encouraged by computational analysis of [3,3]-sigmatropic rearrangements, we can now rapidly synthesize oxa-heterocycles by treating N-phenoxyacetamides (Ph-ONHAc) with compounds containing an sp-hybridized carbon. The generality of the process is illustrated by the late-stage diversification of natural products, including estrone and an approved drug. A combination of experimental and computational studies revealed that the reactions proceed through a facile Claisen-like [3,3]-sigmatropic rearrangement/annulation process.
- Yan, Dingyuan,Jiang, Heming,Sun, Wenxue,Wei, Wei,Zhao, Jing,Zhang, Xinhao,Wu, Yun-Dong
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supporting information
p. 1646 - 1653
(2019/09/04)
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- Rhodium(III)-catalysed cascade [3 + 2] annulation of: N -aryloxyacetamides with 3-(hetero)arylpropiolic acids: Synthesis of benzofuran-2(3 H)-ones
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Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).
- Pan, Jin-Long,Liu, Tuan-Qing,Chen, Chao,Li, Quan-Zhe,Jiang, Wei,Ding, Tong-Mei,Yan, Zhi-Qiang,Zhu, Guo-Dong
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supporting information
p. 8589 - 8600
(2019/10/02)
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- Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization
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A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.
- Pan, Jin-Long,Chen, Chao,Hao, Yu,Liu, Chang,Bai, He-Yuan,Ding, Jun,Zhang, Shu-Yu,Wang, Li-Ren,Xie, Peipei,Xia, Yuanzhi
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supporting information
p. 7131 - 7136
(2018/12/14)
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- Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides
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A Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C-H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization reactions in an efficient manner.
- Wu, Yunxiang,Chen, Zhaoqiang,Yang, Yaxi,Zhu, Weiliang,Zhou, Bing
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supporting information
p. 42 - 45
(2018/01/17)
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- Combination of Cp*RhIII-Catalyzed C?H Activation and a Wagner–Meerwein-Type Rearrangement
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A combination of Cp*RhIII-catalyzed C?H activation and Wagner–Meerwein-type rearrangement was successfully achieved for the first time. Thus, bridged polycyclic molecules that are not readily accessible by other means were accessed under mild c
- Wang, Xiaoming,Lerchen, Andreas,Gensch, Tobias,Knecht, Tobias,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 1381 - 1384
(2017/01/24)
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- Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
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Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.
- Nimmagadda, Sri Krishna,Mallojjala, Sharath Chandra,Woztas, Lukasz,Wheeler, Steven E.,Antilla, Jon C.
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supporting information
p. 2454 - 2458
(2017/02/23)
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- 1. 2 - effinity and ring compound derivative as a preparation for treating myeloma drug application
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The invention discloses a 1,2-oxa-cyclic compound derivative and a preparation method thereof. A molecular structural general formula of 1,2-oxa-cyclic compound derivative is (I), wherein in the formula, A is (hetero) aromatic ring or non-aromatic ring; R
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Paragraph 0085; 0089
(2017/04/28)
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- Rhodium(III)-Catalyzed Annulative Carbooxygenation of 1,1-Disubstituted Alkenes Triggered by C?H Activation
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A Cp*RhIII-catalyzed annulative carbooxygenation of challenging 1,1-disubstituted alkenes triggered by C?H activation of N-aryloxyacetamides has been established, which affords 2,3-dihydrobenzofuran derivatives with a quaternary carbon center i
- Li, Yang,Tang, Yuhai,He, Xin,Shi, Dandan,Wu, Jun,Xu, Silong
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supporting information
p. 7453 - 7457
(2017/06/06)
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- Cp?Rh(III)/Bicyclic Olefin Cocatalyzed C-H Bond Amidation by Intramolecular Amide Transfer
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A bicyclic olefin was discovered as a cocatalyst in a Cp?Rh(III)-catalyzed C-H bond amidation proceeding by an intramolecular amide transfer in N-phenoxyacetamide derivatives. Combining experimental and theoretical studies, we propose that the olefin promotes a Rh(III) intermediate to undergo oxidative addition into the O-N bond to form a Rh(V) nitrenoid species and subsequently direct the nitrenoid to add to the ortho position. The amide directing group plays a dual role as a cleavable coordinating moiety as well as an essential coupling partner for the C-H amidation. This methodology was successfully applied to the late-stage diversification of natural products and a marketed drug under mild conditions.
- Wang, Xiaoming,Gensch, Tobias,Lerchen, Andreas,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 6506 - 6512
(2017/05/17)
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- Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials
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Reported herein is the first example of a transition-metal-catalyzed internal oxidative C-H/C-H cross-coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol-containing natural products, can undergo the coupling with azoles to assemble a large library of highly functionalized 2-(2-hydroxyphenyl)azoles. The route provides an opportunity to rapidly screen white-light-emitting materials. As illustrative examples, two bis(triphenylamine)-bearing 2-(2-hydroxyphenyl)oxazoles, which are difficult to access otherwise, exhibit bright white-light emission, high quantum yield, and thermal stability. Also presented is the first example of the white-light emission, in a single excited-state intramolecular proton transfer system, of 2-(2-hydroxyphenyl)azoles, thus highlighting the charm of C-H activation in the discovery of new organic optoelectronic materials.
- Li, Bijin,Lan, Jingbo,Wu, Di,You, Jingsong
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supporting information
p. 14008 - 14012
(2016/01/25)
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- Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage
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A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.
- Xie, Ying
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supporting information
p. 12372 - 12375
(2016/10/22)
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- Unnatural Amino Acid Synthesis Enabled by the Regioselective Cobalt(III)-Catalyzed Intermolecular Carboamination of Alkenes
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Herein, we report an unprecedented regioselective and entirely atom-economic cobalt(III)-catalyzed method for the non-annulative, intermolecular carboamination of alkenes. The methodology enables the direct synthesis of unnatural amino acid derivatives an
- Lerchen, Andreas,Knecht, Tobias,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 15166 - 15170
(2016/11/25)
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- Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
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The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible-light-mediated electron transfer from novel electron donor-acceptor complexes of the oximes and Et3N was proposed as a key step of this process.
- Davies, Jacob,Booth, Samuel G.,Essafi, Stephanie,Dryfe, Robert A. W.,Leonori, Daniele
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supporting information
p. 14017 - 14021
(2016/01/25)
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- Rh(iii)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates
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Here we report a new and mild Rh(iii)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates. This reaction provided a straightforward way for installing both an α-quaternary carbon center and a free-OH moiety into the phenyl ring, thus giving access to useful 2-(2-hydroxyphenyl)-2-alkoxymalonates with good substrate/functional group tolerance. This journal is
- Zhou, Jie,Shi, Jingjing,Liu, Xuelei,Jia, Jinlong,Song, Huacan,Xu, H. Eric,Yi, Wei
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supporting information
p. 5868 - 5871
(2015/03/30)
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- Potassium tert -butoxide mediated O-arylation of N -hydroxyphthalimide and oximes with diaryliodonium salts
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A metal-free method for the direct O-arylation of N-hydroxyphthalimide, pyridine-2-carboxaldehyde oxime, acetophenone oxime, or dimethylglyoxime with diaryliodonium salts under mild reaction conditions and short reaction time in the presence of potassium tert-butoxide is reported. The diaryliodonium counterion salt plays an important role in the reaction when it is carried out at 40 °C or lower temperatures. Georg Thieme Verlag Stuttgart. New York.
- Misal Castro, Luis C.,Chatani, Naoto
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p. 2312 - 2316
(2014/11/08)
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- NOVEL VASCULAR LEAKAGEAGE INHIBITOR
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The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present invention inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, and enhances the cortical actin ring structure, thereby inhibiting vascular leakage. Accordingly, the vascular leakage inhibitor of the present invention can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present invention is synthesized from commercially available or easily synthesizable pregnenolones, it has remarkably superior feasibility of commercial synthesis.
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Paragraph 0126
(2015/01/07)
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- Rhodium(iii)-catalyzed C-H activation/[4+3] annulation of N-phenoxyacetamides and α,β-unsaturated aldehydes: An efficient route to 1,2-oxazepines at room temperature
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An efficient Rh(iii)-catalyzed coupling reaction of N-phenoxyacetamides with α,β-unsaturated aldehydes to give 1,2-oxazepines via C-H activation/[4+3] annulation has been developed. This transformation does not require oxidants and features C-C/C-N bond formation to yield seven-membered oxazepine rings at room temperature. Further derivation of 1,2-oxazepines leads to important chroman derivatives. This journal is
- Duan, Pingping,Lan, Xia,Chen, Ying,Qian, Shao-Song,Li, Jie Jack,Lu, Liang,Lu, Yanbo,Chen, Bo,Hong, Mei,Zhao, Jing
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supporting information
p. 12135 - 12138
(2014/12/11)
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- Direct detection and reactivity of the short-lived phenyloxenium ion
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Photolysis of protonated phenylhydroxylamine was studied using product analysis, trapping experiments, and laser flash photolysis experiments (UV-vis and TR3 detection) ranging from the femtosecond to the microsecond time scale. We find that the excited state of the photoprecursor is followed by two species: a longer-lived transient (150 ns) that we assign to the phenoxy radical and a shorter-lived (3-20 ns) transient that we assign to the singlet phenyloxenium ion. Product studies from photolysis of this precursor show rearranged protonated o-/p-aminophenols and solvent water adducts (catechol, hydroquinone) and ammonium ion. The former products can be largely ascribed to radical recombination or ion recombination, while the latter are ascribed to solvent water addition to the phenyloxenium ion. The phenyloxenium ion is apparently too short-lived under these conditions to be trapped by external nucleophiles other than solvent, giving only trace amounts of o-/p-chloro adducts upon addition of chloride trap. Product studies upon thermolysis of this precursor give the same products as those generated from photolysis, with the difference being that the ortho adducts (o-aminophenol, hydroquinone) are formed in a higher ratio in comparison to the photolysis products.
- Hanway, Patrick J.,Xue, Jiadan,Bhattacharjee, Ujjal,Milot, Maeia J.,Ruixue, Zhu,Phillips, David Lee,Winter, Arthur H.
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supporting information
p. 9078 - 9082
(2013/07/26)
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- Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity
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Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed C-H functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp=C5Me5). Copyright
- Liu, Guixia,Shen, Yangyang,Zhou, Zhi,Lu, Xiyan
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supporting information
p. 6033 - 6037
(2013/07/19)
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- Rhodium(III)-catalyzed C-H olefination for the Synthesis of ortho-alkenyl phenols using an oxidizing directing group
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By using an oxidizing directing group, a mild, efficient Rh(III) catalyzed C-H olefination reaction between N-phenoxyacetamides and alkenes was developed. This reaction provided a straightforward way for the synthesis of ortho-alkenyl phenols, and the directing group is traceless in the product.
- Shen, Yangyang,Liu, Guixia,Zhou, Zhi,Lu, Xiyan
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supporting information
p. 3366 - 3369
(2013/07/26)
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- AGONISTS OF GPR40
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The present invention relates to compounds that have the ability to modulate the activity of GPR40 and are there-fore useful in the treatment of GPR40 related disorders. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders related to GPR40 activity.
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- Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation
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An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.
- Guru, Murali Mohan,Ali, Md Ashif,Punniyamurthy, Tharmalingam
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scheme or table
p. 5295 - 5308
(2011/08/05)
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- Direct preparation of benzofurans from O-arylhydroxylamines
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Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran derivative via a proposed one-pot condensation-rearrangement- cyclisation reaction sequence in good to excellent yields. Georg Thieme Verlag Stuttgart.
- Contiero, Fanny,Jones, Kevin M.,Matts, Edward A.,Porzelle, Achim,Tomkinson, Nicholas C.O.
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scheme or table
p. 3003 - 3006
(2010/03/03)
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- Inhibitors of transthyretin amyloid fibril formation
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Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.
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Page/Page column 7; 8; sheet 6
(2008/06/13)
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- Bisaryloxime ethers as potent inhibitors of transthyretin amyloid fibril formation
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Amyloid fibril formation by the plasma protein transthyretin (TTR), requiring rate-limiting tetramer dissociation and monomer misfolding, is implicated in several human diseases. Amyloidogenesis can be inhibited through native state stabilization, mediated by small molecule binding to TTR's primarily unoccupied thyroid hormone binding sites. New native state stabilizers have been discovered herein by the facile condensation of arylaldehydes with aryloxyamines affording a bisarylaldoxime ether library. Of the library's 95 compounds, 31 were active inhibitors of TTR amyloid formation in vitro. The bisaryloxime ethers selectively stabilize the native tetrameric state of TTR over the dissociative transition state under amyloidogenic conditions, leading to an increase in the dissociation activation barrier. Several bisaryloxime ethers bind selectively to TTR in human blood plasma over the plethora of other plasma proteins, a necessary attribute for efficacy in vivo. While bisarylaldoxime ethers are susceptible to degradation by N-O bond cleavage, this process is slowed by their binding to TTR. Furthermore, the degradation rate of many of the bisarylaldoxime ethers is slow relative to the half-life of plasma TTR. The bisaryloxime ether library provides valuable structure-activity relationship insight for the development of structurally analogous inhibitors with superior stability profiles, should that prove necessary.
- Johnson, Steven M.,Petrassi, H. Michael,Palaninathan, Satheesh K.,Mohamedmohaideen, Nilofar N.,Purkey, Hans E.,Nichols, Christopher,Chiang, Kyle P.,Walkup, Traci,Sacchettini, James C.,Sharpless, K. Barry,Kelly, Jeffery W.
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p. 1576 - 1587
(2007/10/03)
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- The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines.
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[figure: see text] A novel route to aryloxyamines via the copper-mediated cross-coupling of N-hydroxyphthalimide and phenylboronic acids is reported. The reaction is mediated by selected copper(I) and (II) salts in the presence of pyridine and is tolerant of several functional groups on the phenylboronic acid. The phthallmide group is removed using hydrazine to afford the corresponding aryloxyamine.
- Petrassi,Sharpless,Kelly
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p. 139 - 142
(2007/10/03)
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