Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides

被引：175

作者：

Derosa, Joseph ^{[1
]}

Kleinmans, Roman ^{[1
]}

Tran, Van T. ^{[1
]}

Karunananda, Malkanthi K. ^{[1
]}

Wisniewski, Steven R. ^{[2
]}

Eastgate, Martin D. ^{[2
]}

Engle, Keary M. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA

[2] Bristol Myers Squibb, Chem & Synthet Dev, 1 Squibb Dr, New Brunswick, NJ 08903 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 51期

基金：

美国国家科学基金会;

关键词：

UNACTIVATED OLEFINS; CARBONYL-COMPOUNDS; SUZUKI REACTIONS; CROSS-COUPLINGS; DICARBOFUNCTIONALIZATION; DIFUNCTIONALIZATION; HALIDES;

D O I：

10.1021/jacs.8b11942

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocon-trolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.

引用

页码：17878 / 17883

页数：6

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