Ruphos-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates

被引：53

作者：

van den Hoogenband, Adri ^{[1
]}

Lange, Jos H. M. ^{[1
]}

Terpstra, Jan Willem ^{[1
]}

Koch, Melle ^{[2
]}

Visser, Gerben M. ^{[2
]}

Visser, Martin ^{[1
]}

Korstanje, Ties J. ^{[1
]}

Jastrzebski, Johann T. B. H. ^{[3
]}

机构：

[1] Solvay Pharmaceut, Res Labs, NL-1381 CP Weesp, Netherlands

[2] Wageningen Univ, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands

[3] Univ Utrecht, NL-3584 CH Utrecht, Netherlands

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 26期

关键词：

D O I：

10.1016/j.tetlet.2008.04.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ruphos-mediated Suzuki cross-coupling between (hetero)aryl bromides and secondary alkyltrifluoroborates is described using palladium catalysis. The Ruphos ligand showed superior properties as compared to S-Phos in this type of reaction. This method constitutes a valuable extension to current methods for the straightforward production of secondary-alkylated (hetero)aryl derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4122 / 4124

页数：3

共 73 条

[1] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans
Anderson, Kevin W.
Ikawa, Takashi
Tundel, Rachel E.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) : 10694 - 10695
[2] A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction
Bandgar, BP
Patil, AV
[J]. TETRAHEDRON LETTERS, 2005, 46 (44) : 7627 - 7630
[3] Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides
Barder, TE
Buchwald, SL
[J]. ORGANIC LETTERS, 2004, 6 (16) : 2649 - 2652
[4] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
Barder, TE
Walker, SD
Martinelli, JR
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
[5] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
Bellina, F
Carpita, A
Rossi, R
[J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
[6] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
Billingsley, Kelvin
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) : 3358 - 3366
[7] 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
[8] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
Burgos, Carlos H.
Barder, Timothy E.
Huang, Xiaohua
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4321 - 4326
[9] Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[10] 2-N

← 1 2 3 4 5 6 7 8 →