- Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
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The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
- Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
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p. 9246 - 9250
(2021/12/06)
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- Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
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A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
- Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
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p. 3294 - 3299
(2020/01/21)
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- Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source
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A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.
- Guan, Xinyu,Zhu, Haoran,Zhao, Yingwei,Driver, Tom G.
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- Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant
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Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.
- Shevlin, Michael,Guan, Xinyu,Driver, Tom G.
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p. 5518 - 5522
(2017/08/17)
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- Palladium-Catalyzed Formation of N-Heteroarenes from Nitroarenes using Molybdenum Hexacarbonyl as the Source of Carbon Monoxide
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The development of a method that employs a two-chamber reaction vessel and uses molybdenum hexacarbonyl [Mo(CO)6] as the carbon monoxide (CO) source for the palladium-catalyzed transformation of nitroarenes into indoles or imidazoles is reported.
- Zhou, Fei,Wang, Duo-Sheng,Driver, Tom G.
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p. 3463 - 3468
(2016/01/25)
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- A Scalable Method for Regioselective 3-Acylation of 2-Substituted Indoles under Basic Conditions
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Privileged structures such as 2-arylindoles are recurrent molecular scaffolds in bioactive molecules. We here present an operationally simple, high yielding and scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions
- Johansson, Henrik,Urruticoechea, Andoni,Larsen, Inna,Sejer Pedersen, Daniel
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supporting information
p. 471 - 481
(2015/08/25)
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- Anticonvulsant evaluation of clubbed indole-1,2,4-triazine derivatives: A synthetic approach
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A series of thirty indole C-3 substituted 5-amino-6-(5-substituted-2- phenyl-1H-indol-1-yl)-4,5-dihydro-1,2,4-triazine-3(2H)-thione 5a-f, 6a-f, 7a-f, 8a-f and 9a-f were synthesized to explore prospective anticonvulsant agents. The derivative 1-(1-(5-amino
- Ahuja, Priya,Siddiqui, Nadeem
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p. 509 - 522
(2014/05/20)
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- Palladium-catalyzed synthesis of 3-acylated indoles involving oxidative cross-coupling of indoles with α-amino carbonyl compounds
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A new and selective C-N bond oxidative cleavage method to 3-acylated indoles by Pd-catalyzed oxidative cross coupling of indoles with α-amino carbonyl compounds has been developed; moreover, one-pot synthesis of 3-acylated indoles from 2-ethynylanilines and α-amino carbonyl compounds has also been established. Importantly, the products 3-acylated indoles can be used to construct polyheterocyclic compound, which can be employed as efficient probes for Hg2+ and Fe3+.
- Tang, Ri-Yuan,Guo, Xiao-Kang,Xiang, Jian-Nan,Li, Jin-Heng
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p. 11163 - 11171
(2013/12/04)
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- Copper-catalyzed ortho-halogenation of protected anilines
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A practical Cu-catalyzed direct ortho-halogenation of anilines under aerobic conditions has been developed. The reaction shows typically excellent mono-substitution selectivity, high ortho-regiocontrol and large functional group tolerance.
- Urones, Beatriz,Martinez, Angel Manu,Rodriguez, Nuria,Arrayas, Ramon Gomez,Carretero, Juan C.
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p. 11044 - 11046
(2013/11/19)
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- PROCESSES FOR PREPARING INDOLES
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Methods for the synthesis of an indole in provided. Methods comprise oxidizing a N-aryl imine in the presence of a palladium-based catalyst, an oxidant, and a solvent.
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Paragraph 00102
(2013/07/05)
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- The sequential reactions of tetrazoles with bromoalkynes for the synthesis of (Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides and 2-arylindoles
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2-Arylindoles were prepared by a sequential reaction of Ag-catalyzed α-addition-Pd-catalyzed C-H bond functionalization of tetrazoles with bromoalkynes. A stereocontrolled Ag-catalyzed α-addition reaction of tetrazoles with bromoalkynes underwent smoothly to generate (Z)-N-(2-bromo-1- vinyl)-N-arylcyanamides, which were subsequently converted into 2-arylindoles through an intramolecular cyclization by Pd-catalyzed direct C-H bond functionalizations.
- Zhang, Jiajun,Meng, Ling-Guo,Li, Pinhua,Wang, Lei
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p. 6807 - 6812
(2013/05/23)
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- Intramolecular Ir(I)-catalyzed benzylic C-H bond amination of ortho-substituted aryl azides
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Image Persented Iridium(I) catalyzes the intramolecular benzylic C-H bond amination of ortho-homobenzyl-substituted aryl azides to produce indolines at 25 °C.
- Sun, Ke,Sachwani, Rachna,Richert, Kathleen J.,Driver, Tom G.
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supporting information; experimental part
p. 3598 - 3601
(2011/02/23)
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- Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides
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(Chemical Equation Presented) Azides to indoles: Dirhodium(II)-catalyzed decomposition of aryl azides was developed as a mild, functional group tolerant method for the synthesis of indoles (see scheme).
- Shen, Meihua,Leslie, Brooke E.,Driver, Tom G.
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supporting information; experimental part
p. 5056 - 5059
(2009/03/11)
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- An annulative approach to highly substituted indoles: Unusual effect of phenolic additives on the success of the arylation of ketone enolates
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A novel palladium-catalyzed arylation of ketone enolates with o-nitrohaloarenes was achieved through the addition of phenol additives. The mild reaction conditions employed allowed for the inclusion of a wide variety of functional groups in both substrates to be tolerated. The products of this reaction were then readily reductively cyclized to give highly substituted indoles in moderate to excellent overall yields. Copyright
- Rutherford, Jennifer L.,Rainka, Matthew P.,Buchwald, Stephen L.
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p. 15168 - 15169
(2007/10/03)
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