A Versatile Catalyst System for Suzuki-Miyaura Cross-Coupling Reactions of C(sp2)-Tosylates and Mesylates

被引：111

作者：

Bhayana, Brijesh ^{[1
]}

Fors, Brett P. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 17期

基金：

美国国家卫生研究院;

关键词：

ARYL TOSYLATES; BORONIC ACIDS; HALIDES; ESTERS;

D O I：

10.1021/ol9015892

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl and vinyl tosylates and mesylates has been developed. This catalyst displays excellent functional group tolerance and allows the coupling of heteroarylboronic acids with aryl tosylates and mesylates to be performed in high yields. Moreover, reactions employing alkylboronic acids, as well as heteroaryl, vinyl, and allylic pinacol boronate esters, were conducted with high efficiencies.

引用

页码：3954 / 3957

页数：4

共 20 条

[1] Ackermann L., 2008, ANGEW CHEM, V121, P207
[2] An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane
Billingsley, Kelvin L.
Buchwald, Stephen L.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) : 5589 - 5591
[3] A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles
Billingsley, Kelvin L.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4695 - 4698
[4] Phosphaadamantanes as ligands for palladium catalyzed cross-coupling chemistry:: Library synthesis, characterization, and screening in the Suzuki coupling of alkyl halides and tosylates containing β-hydrogens with boronic acids and alkylboranes
Brenstrum, T
Gerristma, DA
Adjabeng, GM
Frampton, CS
Britten, J
Robertson, AJ
McNulty, J
Capretta, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) : 7635 - 7639
[5] Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates
Deng, James Z.
Paone, Daniel V.
Ginnetti, Anthony T.
Kurihara, Hideki
Dreher, Spencer D.
Weissman, Steven A.
Stauffer, Shaun R.
Burgey, Christopher S.
[J]. ORGANIC LETTERS, 2009, 11 (02) : 345 - 347
[6] Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation
Dreher, Spencer D.
Dormer, Peter G.
Sandrock, Deidre L.
Molander, Gary A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9257 - +
[7] A highly active catalyst for Pd-catalyzed amination reactions: Cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides
Fors, Brett P.
Watson, Donald A.
Biscoe, Mark R.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) : 13552 - +
[8] Preparation of enamides via palladium-catalyzed amidation of enol tosylates
Klapars, A
Campos, KR
Chen, CY
Volante, RP
[J]. ORGANIC LETTERS, 2005, 7 (06) : 1185 - 1188
[9] A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates
Knapp, David M.
Gillis, Eric P.
Burke, Martin D.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) : 6961 - +
[10] N-Heterocyclic Carbene Derived Nickel-Pincer Complexes: Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates
Kuroda, Jun-ichi
Inamoto, Kiyofumi
Hiroya, Kou
Doi, Takayuki
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (14) : 2251 - 2261

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