cas 6165-69-1, 3-Thiopheneboronic acid | Articles data

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Thiophene-derivatized Pybox and its highly luminescent lanthanide ion complexes
A new complex of 4-thiophen-3-yl-pyridine-2,6-bis(oxazoline) with Eu(III) triflate has been isolated. This complex and its Tb(III) analogue are luminescent in the solid state. The complexes dissolve with partial retention of the solid-state structure in acetonitrile to yield highly luminescent solutions with quantum yields of 76.2 and 58.6% for red and green emission, respectively. Copyright
De Bettencourt-Dias, Ana,Viswanathan, Subha,Rollett, Alexandra
p. 15436 - 15437
(2007)
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Synthesis and utility of 3-silylthiophenes having perfluoroalkyl groups
The synthesis of a novel class of 3-silyl substituted thiophenes possessing perfluoroalkyl groups on the silicon atom was investigated. The treatment of 3-bromothiophene with n-butyllithium followed by the reaction with halosilanes proceeded to afford the corresponding 3-silyl substituted thiophenes 1 in good yields. The chemical polymerization of the resulting 1 did not work well. However, the electropolymerization of 3-silylthiophenes 1a and 1b provided the corresponding polymers 5a and 5b with head-to-tail regioregularity. The cyclic voltammogram of the resulting polymers 5a and 5b indicated both n- and p-doping properties.
Honda, Mitsunori,Taniguchi, Yusuke,Hayashi, Tomohiro,Kunimoto, Ko-Ki,Segi, Masahito,Yamaguchi, Takahiro
p. 4554 - 4558
(2017)
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Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup
p. 10966 - 10972
(2020/09/23)

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates
Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.
Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong
p. 4253 - 4257
(2018/09/18)

An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10
An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.
Silva, Renato L.,Santos, Cosme S.,Santos, Jonh A. M.,Oliveira, Roberta A.,Menezes, Paulo H.,Freitas, Juliano C. R.
p. 1777 - 1785
(2018/09/04)

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure
The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.
Smith, Michael J.,Lawler, Michael J.,Kopp, Nathaniel,McLeod, Douglas D.,Davulcu, Akin H.,Lin, Dong,Katipally, Kishta,Sfouggatakis, Chris
p. 1859 - 1863
(2017/11/24)

Covalent functionalization of graphene with polythiophene through a Suzuki coupling reaction
In our tentative previous work, graphene was covalently functionalized by hexylbenzene and poly(9,9-dihexylfluorene) (PF) through a Suzuki coupling reaction. In this paper, thiophene and polythiophene (PTH) were grafted to brominated graphene (Br-Gra) in the same polymeric method. The obtained conjugated system of modified graphene was characterized by various techniques, including Fourier transform-infrared (FT-IR), ultraviolet-vis (UV-vis), thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), fluorescence emission spectra, 1H-NMR spectra, and Raman spectroscopy. All the results revealed that thiophene and PTH were successfully grafted to the graphene. What's more, a colour change of their solution (Br-Gra doesn't dissolve in THF, while both thiophene grafted graphene (Gra-3TH) and PTH grafted graphene (Gra-PT) dissolve in THF, and exhibit a black and green color in THF respectively), which is caused by an electron-energy transfer between graphene and the conjugated polymer was also observed. These polymeric conjugated systems of modified graphene materials may open an interesting field for the application of graphene in photoelectric devices.
Yao, Yanjin,Gao, Jie,Bao, Feng,Jiang, Sanfeng,Zhang, Xu,Ma, Rui
p. 42754 - 42761
(2015/05/27)

Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand
The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh) 3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by Hbonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′- and 8,8′-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7′-positions have the biggest impact in a positive direction. VANOL destination: The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate; see figure) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Copyright
Guan, Yong,Ding, Zhensheng,Wulff, William D.
supporting information
p. 15565 - 15571
(2013/11/19)

Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]
Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.
Molander, Gary A.,Cavalcanti, Livia N.,Garcia-Garcia, Carolina
p. 6427 - 6439
(2013/07/26)

On the directing effect of boronate groups in the lithiation of boronated thiophenes
An investigation of thiophene boronates has revealed the usefulness of a metalation reaction in the synthesis of various lithiated thiophene boronates, which were further converted to functionalized thiopheneboronic derivatives. The lithiation of 2- and 3-thienylboronic N-butyldiethanolamine (BDEA) esters with lithium diisopropylamide and lithium 2,2,6,6-tetramethylpiperidide showed that both boronated thiophenes were readily deprotonated. In the latter case, lithiation at the 2-position adjacent both to sulfur and the borocanyl group is thermodynamically favoured due to the significant stabilizing effect of the borocanyl group. Further derivatization with a range of electrophiles followed by hydrolysis afforded various 2-substituted 3-thiopheneboronic acids. Lithiation of the corresponding thiopheneboronic "ate" complexes of the type [ThB(OR)3]Li revealed that the 2-thienyl derivatives could not be effectively deprotonated, whereas the "ate" complex, [3-ThB(OEt)3]Li, was selectively lithiated with nBuLi at C-2. This points to a directing effect of the anionic boronate moiety. The resulting bimetallic species, [(2-Li-3-Th)B(OEt)3]Li, underwent ring-closing dimerization upon heating to give, after subsequent hydrolysis, 4,8-dihydro-4,8-dihydroxy-p-diborino[2,3-b:5,6-b′]dithiophene - a cyclic diborinic acid. A computational study of the lithiation of boronated thiophenes and furans proved that boronation decreases ring-proton acidity. This effect is much stronger for the boronic "ate" complexes than for the corresponding neutral BDEA esters. Calculations of the transition states have shown that the specific directing effect of boronate groups in 3-thienyl derivatives is due to intramolecular oxygen-lithium coordination.
Borowska, Elena,Durka, Krzysztof,Lulinski, Sergiusz,Serwatowski, Janusz,Wozniak, Krzysztof
scheme or table
p. 2208 - 2218
(2012/06/01)

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener
The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.
Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.
supporting information
p. 4814 - 4817,4
(2012/12/12)

Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges
A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.
Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise
supporting information; experimental part
p. 4479 - 4481
(2011/10/09)

Lithium aminoborohydrides 17. Palladium catalyzed borylation of aryl iodides, bromides, and triflates with diisopropylaminoborane prepared from lithium diisopropylaminoborohydride
The Alcaraz-Vaultier borylation of aryl halides and triflates is reported utilizing diisopropylaminoborane (BH2N(iPr)2) prepared from the corresponding lithium aminoborohydride (LAB reagent). BH 2N(iPr)2, prepared by reacting lithium diisopropylaminoborohydride with trimethylsilyl chloride, provided the most consistent isolated yields from this reaction. Catalytic amounts of palladium dichloride produced the highest yields from aryl iodides, while catalytic tris(dibenzylideneacetone)dipalladium(chloroform) provided the best yields for aryl bromides and triflates. This route to boronic acids is mild enough to tolerate various functionalities and for the first time employs aryl triflates as substrates for the Alcaraz-Vaultier borylation. In addition, it was found that both boronic acid and ester compounds could be isolated from the reaction mixture utilizing simple work-up procedures. Treatment of the reaction intermediate with an acid/base work-up provided the corresponding boronic acid, while treating the same intermediate with a diol, such as neopentyl glycol, afforded the corresponding boronic ester.
Haddenham, Dustin,Bailey, Christopher L.,Vu, Chau,Nepomuceno, Gabby,Eagon, Scott,Pasumansky, Lubov,Singaram, Bakthan
experimental part
p. 576 - 583
(2011/03/18)

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
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(2011/09/15)

Efficient hydrolysis of organotrifluoroborates via silica gel and water
(Chemical Equation Presented) A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates.As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters. 2009 American Chemical Society.
Molander, Gary A.,Cavalcanti, Livia N.,Canturk, Belgin,Pan, Po-Shen,Kennedy, Lauren E.
supporting information; experimental part
p. 7364 - 7369
(2010/01/16)

Pyridine-bis (oxazoline)("pybox") moiety as a chelator and sensitizer for lanthanide Ion (Ln (III)) luminescence
This invention relates to novel Ln(III) complexes of pybox, and methods of making the same. The present invention also relates to a method of use of pybox as a chelating moiety and sensitizer for Ln(III) ion luminescence. Derivatives of pybox and methods of making the same are also provided.
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(2009/12/04)

SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.
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(2010/02/12)

5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6
A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6. The inhibitory activity of the most potent CYP2A6 inhibitors on the functional activity of human cytochrome P450s 3A4, 2E1, 2B6, 2C9, 2C19, and 2D6 was also examined to determine inhibitor selectivity. We identified 36 compounds that were more potent than nicotine at inhibition of coumarin 7-hydroxylase (CYP2A6) activity. We also found a number of compounds to be highly selective for the inhibition of human CYP2A6 versus the other human CYPs examined.
Denton, Travis T.,Zhang, Xiaodong,Cashman, John R.
p. 224 - 239
(2007/10/03)

N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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Page column 77

(2010/01/30)

An improved protocol for the preparation of 3-pyridyl- and some arylboronic acids
3-Pyridylboronic acid was prepared in high yield and bulk quantity from 3-bromopyridine via a protocol of lithium-halogen exchange and "in situ quench". This technique was further studied and evaluated on other aryl halides in the preparation of arylboronic acids.
Li, Wenjie,Nelson, Dorian P.,Jensen, Mark S.,Hoerrner, R. Scott,Cai, Dongwei,Larsen, Robert D.,Reider, Paul J.
p. 5394 - 5397
(2007/10/03)

Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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(2008/06/13)

THIENYL-, FURYL- AND PYRROLYL SULFONAMIDES AND DERIVATIVES THEREOF THAT MODULATE THE ACTIVITY OF ENDOTHELIN
Thienyl-, furyl-and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl) furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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(2008/06/13)

SULFONAMIDES AND DERIVATIVES THEREOF THAT MODULATE THE ACTIVITY OF ENDOTHELIN
Sulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided. The sulfonamides have formula I: STR1 in which Ar 1 is a 3-or 5-isoxazolyl and Ar. sup.2 is selected from among alkyl, including straight and branched chains, aromatic rings, fused aromatic rings and heterocyclic rings, including 5-membered heterocycles with one, two or more heteroatoms and fused ring analogs thereof and 6-membered rings with one, two or more heteroatoms and fused ring analogs thereof. Ar 2 is preferably thiophenyl, furyl, pyrrolyl, naphthyl, and phenyl. Compounds in which Ar. sup.1 is a 4-halo-substituted isoxazole are more active than the corresponding alkyl-substituted compound and compounds in which Ar 1 is substituted at this position with a higher alkyl tend to exhibit greater affinity for ET B receptors than the corresponding lower alkyl-substituted compound.
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(2008/06/13)