Ligand-Promoted Borylation of C(sp3)-H Bonds with Palladium(II) Catalysts

被引:115
作者
He, Jian [1 ]
Jiang, Heng [1 ]
Takise, Ryosuke [1 ]
Zhu, Ru-Yi [1 ]
Chen, Gang [1 ]
Dai, Hui-Xiong [1 ]
Dhar, T. G. Murali [2 ]
Shi, Jun [3 ]
Zhang, Hao [3 ]
Cheng, Peter T. W. [3 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Bristol Myers Squibb Co, Discovery Chem, Princeton, NJ 08543 USA
[3] Bristol Myers Squibb Co, Discovery Chem, Pennington, NJ 08534 USA
基金
美国国家科学基金会;
关键词
C-H BORYLATION; CROSS-COUPLING REACTIONS; ARYL CHLORIDES; ROOM-TEMPERATURE; AROMATIC BORYLATION; ARENES; FUNCTIONALIZATION; ESTERS; ACIDS; DERIVATIVES;
D O I
10.1002/anie.201509996
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A quinoline-based ligand effectively promotes the palladium-catalyzed borylation of C(sp(3))-H bonds. Primary beta-C(sp(3))-H bonds in carboxylic acid derivatives as well as secondary C(sp(3))-H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and cycloheptanes, can thus be borylated. This directed borylation method complements existing iridium(I)-and rhodium(I)-catalyzed C-H borylation reactions in terms of scope and operational conditions.
引用
收藏
页码:785 / 789
页数:5
相关论文
共 68 条
[1]  
[Anonymous], 2011, Angewandte Chemie International Edition, DOI DOI 10.1002/ANGE.201104544
[2]  
[Anonymous], ANGEW CHEM
[3]   Inversion or Retention? Effects of Acidic Additives on the Stereochemical Course in Enantiospecific Suzuki-Miyaura Coupling of α-(Acetylamino)benzylboronic Esters [J].
Awano, Tomotsugu ;
Ohmura, Toshimichi ;
Suginome, Michinori .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) :20738-20741
[4]  
Billingsley K.L., 2007, ANGEW CHEMIE, V119, P5455
[5]   An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane [J].
Billingsley, Kelvin L. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5589-5591
[6]   Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies [J].
Billingsley, Kelvin L. ;
Barder, Timothy E. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5359-5363
[7]   Silyl-directed, iridium-catalyzed ortho-borylation of arenes. A one-pot ortho-borylation of phenols, arylamines, and alkylarenes [J].
Boebel, Timothy A. ;
Hartwig, John. F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7534-+
[8]  
Chen HY, 1999, ANGEW CHEM INT EDIT, V38, P3391, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3391::AID-ANIE3391>3.0.CO
[9]  
2-N
[10]   Thermal, catalytic, regiospecific functionalization of alkanes [J].
Chen, HY ;
Schlecht, S ;
Semple, TC ;
Hartwig, JF .
SCIENCE, 2000, 287 (5460) :1995-1997