Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides

被引：44

作者：

Hofstra, Julie L. ^{[1
]}

Poremba, Kelsey E. ^{[1
]}

Shimozono, Alex M. ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 42期

基金：

美国国家科学基金会;

关键词：

alkenes; halides; kinetics; nickel; reaction mechanisms; VINYL HALIDES; TRANSITION-METAL; HALOGEN EXCHANGE; ARYL; ALKYNES; TRIFLUOROMETHYLTHIOLATION; CHLORIDES; BROMIDES;

D O I：

10.1002/anie.201906815

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)(2).4 H2O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine.

引用

页码：14901 / 14905

页数：5

共 50 条

[1] RECENT APPLICATIONS OF THE SHAPIRO REACTION [J].

ADLINGTON, RM ;

BARRETT, AGM .

ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) :55-59

[2]

[Anonymous], 1996, NATURALLY OCCURRING

[3] Oxidative Addition of Aryl Electrophiles to a Prototypical Nickel(0) Complex: Mechanism and Structure/Reactivity Relationships [J].

Bajo, Sonia ;

Laidlaw, Gillian ;

Kennedy, Alan R. ;

Sproules, Stephen ;

Nelson, David J. .

ORGANOMETALLICS, 2017, 36 (08) :1662-1672

[4] A NEW REACTION OF HYDRAZONES [J].

BARTON, DHR ;

OBRIEN, RE ;

STERNHELL, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (FEB) :470-&

[5] Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species [J].

Beromi, Megan Mohadjer ;

Nova, Ainara ;

Balcells, David ;

Brasacchio, Ann M. ;

Brudvig, Gary W. ;

Guard, Louise M. ;

Hazari, Nilay ;

Vinyard, David J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (02) :922-936

[6] Kinetic Profiling of Catalytic Organic Reactions as a Mechanistic Tool [J].

Blackmond, Donna G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (34) :10852-10866

[7] VINYLIC ORGANOBORANES .13. A CONVENIENT STEREOSPECIFIC SYNTHESIS OF (Z)-1-HALO-1-ALKENES FROM 1-ALKYNES VIA (E)-1-ALKENYLBORANE DERIVATIVES WITH HALOGENS [J].

BROWN, HC ;

SUBRAHMANYAM, C ;

HAMAOKA, T ;

RAVINDRAN, N ;

BOWMAN, DH ;

MISUMI, S ;

UNNI, MK ;

SOMAYAJI, V ;

BHAT, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6068-6075

[8] VINYL-LITHIUM REAGENTS FROM ARENESULFONYLHYDRAZONES [J].

CHAMBERLIN, AR ;

STEMKE, JE ;

BOND, FT .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :147-154

[9] 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

[10]

De Meijer A.D., 2004, Metal-catalyzed crosscoupling reactions, V2

← 1 2 3 4 5 →