Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes

被引:104
作者
Logan, Kaitlyn M. [1 ]
Sardini, Stephen R. [1 ]
White, Sean D. [1 ]
Brown, M. Kevin [1 ]
机构
[1] Indiana Univ, Dept Chem, 800 East Kirkwood Ave, Bloomington, IN 47405 USA
关键词
CROSS-COUPLING REACTIONS; BORYLATIVE EXO-CYCLIZATION; ENANTIOSELECTIVE ARYLBORATION; COPPER(I)-CATALYZED REACTION; REGIOSELECTIVE ARYLBORATION; 3-COMPONENT CARBOBORATION; ORGANOMETALLIC REAGENTS; COOPERATIVE CATALYSIS; SYNERGISTIC CATALYSIS; ASYMMETRIC-SYNTHESIS;
D O I
10.1021/jacs.7b12160
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Ni-catalyzed method for arylboration is disclosed. The method allows for highly stereoselective arylboration of unactivated alkenes. The reactions utilize a simple Ni-catalyst and work with a broad range of alkenes and aryl bromides. The products represent useful intermediates for chemical synthesis due to the versatility of the C-B bond. Preliminary mechanistic details of the method are also disclosed.
引用
收藏
页码:159 / 162
页数:4
相关论文
共 54 条
[1]   Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes [J].
Butcher, Trevor W. ;
McClain, Edward J. ;
Hamilton, Tyler G. ;
Perrone, Trina M. ;
Kroner, Kayla M. ;
Donohoe, Gregory C. ;
Akhmedov, Novruz G. ;
Petersen, Jeffrey L. ;
Popp, Brian V. .
ORGANIC LETTERS, 2016, 18 (24) :6428-6431
[2]   Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence [J].
Chen, Bin ;
Cao, Peng ;
Yin, Xuemei ;
Liao, Yang ;
Jiang, Liyin ;
Ye, Jialin ;
Wang, Min ;
Liao, Jian .
ACS CATALYSIS, 2017, 7 (04) :2425-2429
[3]   Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652
[4]   Diastereoselective Construction of Functionalized Homoallylic Alcohols by Ni-Catalyzed Diboron-Promoted Coupling of Dienes and Aldehydes [J].
Cho, Hee Yeon ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) :16140-+
[5]   Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes [J].
Coombs, John R. ;
Morken, James P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) :2636-2649
[6]   Nickel-Catalyzed Borylative Ring Opening of Vinyl Epoxides and Aziridines [J].
Crotti, Stefano ;
Bertolini, Ferruccio ;
Macchia, Franco ;
Pineschi, Mauro .
ORGANIC LETTERS, 2009, 11 (16) :3762-3765
[7]   Nickel-Catalyzed Cyclizative trans-Carboboration of Alkynes through Activation of Boron-Chlorine Bonds by Using Organometallic Reagents as Donors of Organic Groups [J].
Daini, Masaki ;
Yamamoto, Akihiko ;
Suginome, Michinori .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (11) :968-976
[8]   Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling [J].
Derosa, Joseph ;
Tran, Van T. ;
Boulous, Mark N. ;
Chen, Jason S. ;
Engle, Keary M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (31) :10657-10660
[9]   Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon-Boron Bonds [J].
Dudnik, Alexander S. ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10693-10697
[10]   Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes [J].
Garcia-Dominguez, Andres ;
Li, Zhaodong ;
Nevado, Cristina .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (20) :6835-6838