共 27 条
Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis
被引:226
作者:

DeLano, Travis J.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

Reisman, Sarah E.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
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

Anka-Lufford, Lukiana L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Huihui, Kierra M. M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Gower, Nicholas J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Ackerman, Laura K. G.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Weix, Daniel J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[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

Cherney, Alan H.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

Reisman, Sarah E.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
[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

Cherney, Alan H.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

Kadunce, Nathaniel T.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

Reisman, Sarah E.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
[4]
COUPLING OF ARYL CHLORIDES BY NICKEL AND REDUCING METALS
[J].
COLON, I
;
KELSEY, DR
.
JOURNAL OF ORGANIC CHEMISTRY,
1986, 51 (14)
:2627-2637

COLON, I
论文数: 0 引用数: 0
h-index: 0

KELSEY, DR
论文数: 0 引用数: 0
h-index: 0
[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

CONAN, A
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE

SIBILLE, S
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE

DINCAN, E
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE

PERICHON, J
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE CNRS,ELECTROCHIM CATALYSE SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE
[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

Duan, Zhengli
论文数: 0 引用数: 0
h-index: 0
机构:
Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

Li, Wu
论文数: 0 引用数: 0
h-index: 0
机构:
Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

Lei, Aiwen
论文数: 0 引用数: 0
h-index: 0
机构:
Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[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

Durandetti, M
论文数: 0 引用数: 0
h-index: 0
机构: Lab. d'Electrochimie, Catalys. S., UMR 28 CNRS, 94320 Thiais, 2, rue Henri-Dunant

Nedelec, JY
论文数: 0 引用数: 0
h-index: 0
机构: Lab. d'Electrochimie, Catalys. S., UMR 28 CNRS, 94320 Thiais, 2, rue Henri-Dunant

Perichon, J
论文数: 0 引用数: 0
h-index: 0
机构: Lab. d'Electrochimie, Catalys. S., UMR 28 CNRS, 94320 Thiais, 2, rue Henri-Dunant
[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

Durandetti, M
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthese, UMR 28 CNRS, 94320 Thiais, 2, rue Henri-Dunant

Perichon, J
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthese, UMR 28 CNRS, 94320 Thiais, 2, rue Henri-Dunant

Nedelec, JY
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthese, UMR 28 CNRS, 94320 Thiais, 2, rue Henri-Dunant
[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

DURANDETTI, M
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthèse Organique, CNRS, UMR 28, 2, Rue Henri Dunant

SIBILLE, S
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthèse Organique, CNRS, UMR 28, 2, Rue Henri Dunant

NEDELEC, JY
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthèse Organique, CNRS, UMR 28, 2, Rue Henri Dunant

PERICHON, J
论文数: 0 引用数: 0
h-index: 0
机构: Laboratoire d'Electrochimie, Catalyse et Synthèse Organique, CNRS, UMR 28, 2, Rue Henri Dunant
[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

Everson, Daniel A.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Weix, Daniel J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA