Palladium(0)-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides

被引:62
作者
Molander, Gary A. [1 ]
Fumagalli, Tiziano [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
关键词
ARYLBORONIC ACIDS; ARYL CHLORIDES; LIGANDLESS PALLADIUM; ALKYL BROMIDES; CATALYSTS; AMINATION;
D O I
10.1021/jo0608366
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient palladium(0)-catalyzed Suzuki-Miyaura cross-couplings are described. The reactions involving potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides can generally be carried out using <= 2 mol % of palladium catalyst and 3 equiv of base in toluene/H2O. When stereodefined alkenyl bromides are employed, the resulting styrene derivatives are accessed stereospecifically. A variety of functional groups are tolerated in both coupling partners.
引用
收藏
页码:5743 / 5747
页数:5
相关论文
共 58 条
[51]   Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement [J].
Toyota, M ;
Asano, T ;
Ihara, M .
ORGANIC LETTERS, 2005, 7 (18) :3929-3932
[52]   Asymmetric memory at labile, stereogenic boron: Enolate alkylation of oxazaborolidinones [J].
Vedejs, E ;
Fields, SC ;
Hayashi, R ;
Hitchcock, SR ;
Powell, DR ;
Schrimpf, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2460-2470
[53]   CONVERSION OF ARYLBORONIC ACIDS INTO POTASSIUM ARYLTRIFLUOROBORATES - CONVENIENT PRECURSORS OF ARYLBORON DIFLUORIDE LEWIS-ACIDS [J].
VEDEJS, E ;
CHAPMAN, RW ;
FIELDS, SC ;
LIN, S ;
SCHRIMPF, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3020-3027
[54]   Highly active palladium catalysts for Suzuki coupling reactions [J].
Wolfe, JP ;
Singer, RA ;
Yang, BH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9550-9561
[55]   Ligand promoted palladium-catalyzed homo-coupling of arylboronic acids [J].
Wong, MS ;
Zhang, XL .
TETRAHEDRON LETTERS, 2001, 42 (24) :4087-4089
[56]   A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: Novel ligand coordination [J].
Yin, JJ ;
Rainka, MP ;
Zhang, XX ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1162-1163
[57]   Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates [J].
Yuen, AKL ;
Hutton, CA .
TETRAHEDRON LETTERS, 2005, 46 (46) :7899-7903
[58]   Palladium-imidazol-2-ylidene complexes as catalysts for facile and efficient Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids [J].
Zhang, CM ;
Huang, JK ;
Trudell, ML ;
Nolan, SP .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3804-3805