Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

被引:226
作者
DeLano, Travis J. [1 ]
Reisman, Sarah E. [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
基金
美国国家科学基金会;
关键词
nickel; electrochemistry; enantioselective; cross-coupling; asymmetric catalysis; ARYL HALIDES;
D O I
10.1021/acscatal.9b01785
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An electrochemically driven enantioselective nickel-catalyzed reductive cross-coupling of alkenyl bromides and benzyl chlorides is reported. The reaction forms products bearing allylic stereogenic centers with good enantioselectivity under mild conditions in an undivided cell. Electrochemical activation and turnover of the catalyst mitigate issues posed by metal powder reductants. This report demonstrates that enantioselective Ni-catalyzed cross-electrophile couplings can be driven electrochemically.
引用
收藏
页码:6751 / 6754
页数:7
相关论文
共 27 条
[1]   Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents [J].
Anka-Lufford, Lukiana L. ;
Huihui, Kierra M. M. ;
Gower, Nicholas J. ;
Ackerman, Laura K. G. ;
Weix, Daniel J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (33) :11564-11567
[2]   Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles [J].
Cherney, Alan H. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14365-14368
[3]   Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445
[4]   COUPLING OF ARYL CHLORIDES BY NICKEL AND REDUCING METALS [J].
COLON, I ;
KELSEY, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2627-2637
[5]   NICKEL-CATALYZED ELECTROREDUCTIVE COUPLING OF ALPHA-HALOGENOESTERS WITH ARYL OR VINYL HALIDES [J].
CONAN, A ;
SIBILLE, S ;
DINCAN, E ;
PERICHON, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :48-49
[6]   Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant [J].
Duan, Zhengli ;
Li, Wu ;
Lei, Aiwen .
ORGANIC LETTERS, 2016, 18 (16) :4012-4015
[7]   Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides [J].
Durandetti, M ;
Nedelec, JY ;
Perichon, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1748-1755
[8]   Asymmetric induction in the electrochemical cross-coupling of aryl halides with alpha-chloropropionic acid derivatives catalyzed by nickel complexes [J].
Durandetti, M ;
Perichon, J ;
Nedelec, JY .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :7914-7915
[9]   A NOVEL METHOD OF ARYLATION OF ALPHA-CHLOROKETONES [J].
DURANDETTI, M ;
SIBILLE, S ;
NEDELEC, JY ;
PERICHON, J .
SYNTHETIC COMMUNICATIONS, 1994, 24 (02) :145-151
[10]   Cross-Electrophile Coupling: Principles of Reactivity and Selectivity [J].
Everson, Daniel A. ;
Weix, Daniel J. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :4793-4798