Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways

被引:483
作者
Chen, Xiao [1 ]
Goodhue, Charles E. [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Brandeis Univ, Dept Chem MS015, Waltham, MA 02454 USA
基金
美国国家科学基金会;
关键词
D O I
10.1021/ja0646747
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner. Copyright © 2006 American Chemical Society.
引用
收藏
页码:12634 / 12635
页数:2
相关论文
共 34 条
[1]   Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]  
[Anonymous], 2005, HDB C H TRANSFORMATI
[3]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[4]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[5]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[6]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
[7]   1,4-Palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles [J].
Campo, MA ;
Huang, QH ;
Yao, TL ;
Tian, QP ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11506-11507
[8]   A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].
Catellani, M ;
Frignani, F ;
Rangoni, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122
[9]   Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].
Chen, X ;
Li, JJ ;
Hao, XS ;
Goodhue, CE ;
Yu, JQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79
[10]   C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4 [J].
Dangel, BD ;
Godula, K ;
Youn, SW ;
Sezen, B ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11856-11857