Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): new electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions

被引：21

作者：

Joseph, Jayan T. ^{[1
,2
]}

Sajith, Ayyiliath M. ^{[2
]}

Ningegowda, Revanna C. ^{[2
]}

Nagaraj, Archana ^{[2
]}

Rangappa, K. S. ^{[1
]}

Shashikanth, Sheena ^{[1
]}

机构：

[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India

[2] Syngene Int Ltd, Bangalore 560099, Karnataka, India

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 36期

关键词：

Pentafluorobenzenesulfonates; Cross-coupling; Palladium; Suzuki-Miyaura cross-coupling; GENERAL PALLADIUM CATALYST; LIGAND-FREE; C-C; ARYL; REAGENTS; DERIVATIVES; POTASSIUM; HALIDES; ACIDS; VINYL;

D O I：

10.1016/j.tetlet.2015.07.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5106 / 5111

页数：6

共 50 条

[1] Aryl and heteroaryl nosylates as stable and cheap partners for Suzuki-Miyaura cross-coupling reactions
Dikova, Anna
Cheval, Nicolas P.
Blanc, Aurelien
Weibel, Jean-Marc
Pale, Patrick
[J]. TETRAHEDRON, 2016, 72 (16) : 1960 - 1968
[2] Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
Molander, Gary A.
Brown, Adam R.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9681 - 9686
[3] Suzuki-Miyaura Cross-Coupling of Potassium Dioxolanylethyltrifluoroborate and Aryl/Heteroaryl Chlorides
Fleury-Bregeot, Nicolas
Oehlrich, Daniel
Rombouts, Frederik
Molander, Gary A.
[J]. ORGANIC LETTERS, 2013, 15 (07) : 1536 - 1539
[4] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds
Billingsley, Kelvin L.
Anderson, Kevin W.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) : 3484 - 3488
[5] A highly active catalytic system for Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water
Mao, Shu-Lan
Sun, Yue
Yu, Guang-Ao
Zhao, Cui
Han, Zhi-Jun
Yuan, Jia
Zhu, Xiaolei
Yang, Qihua
Liu, Sheng-Hua
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (47) : 9410 - 9417
[6] Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides
Dreher, Spencer D.
Lim, Siang-Ee
Sandrock, Deidre L.
Molander, Gary A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3626 - 3631
[7] Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate
Kassel, Vincent M.
Hanneman, Christopher M.
Delaney, Connor P.
Denmark, Scott E.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (34) : 13845 - 13853
[8] Conjugated Polymer Nanoparticles by Suzuki-Miyaura Cross-Coupling Reactions in an Emulsion at Room Temperature
Muenmart, Duangratchaneekorn
Foster, Andrew B.
Harvey, Alan
Chen, Ming-Tsz
Navarro, Oscar
Promarak, Vinich
McCairn, Mark C.
Behrendt, Jonathan M.
Turner, Michael L.
[J]. MACROMOLECULES, 2014, 47 (19) : 6531 - 6539
[9] New Tricyclic Aryl Quinazoline Derivatives by Suzuki-Miyaura Cross-Coupling
Elmuradov, Burkhon
Okmanov, Rasul
Juraev, Bakhromjon
Draeger, Gerald
Butenschoen, Holger
[J]. CHEMISTRYOPEN, 2024,
[10] Ferrocenylmethylphosphines as ligands for room temperature Ni(0)-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl arenesulfonates and aryl chlorides
Tang, ZY
Spinella, S
Hu, QS
[J]. TETRAHEDRON LETTERS, 2006, 47 (14) : 2427 - 2430

← 1 2 3 4 5 →