Arylation of Aldehydes To Directly Form Ketones via Tandem Nickel Catalysis

被引：30
|
作者：
Lei, Chuanhu [2 ,3 ]
Zhu, Daoyong [4 ]
Tangcueco, Vicente I. I. I. Tiu [4 ]
Zhou, Jianrong Steve [1 ]
机构：
[1] Peking Univ, Sch Chem Biol & Biotechnol, State Key Lab Chem Oncogen, Key Lab Chem Genom,Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[2] Shanghai Univ, Coll Sci, Ctr Supramol Chem & Catalysis, Shanghai 200444, Peoples R China
[3] Shanghai Univ, Coll Sci, Dept Chem, Shanghai 200444, Peoples R China
[4] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 15期
关键词：
C-H BOND; ARYLBORONIC ACIDS; COUPLING REACTION; AROMATIC-ALDEHYDES; DIARYL KETONES; ARYL IODIDES; COMPLEXES; TRANSFORMATION; DEOXYGENATION; ALKYLATION;
D O I：
10.1021/acs.orglett.9b01782
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves alpha-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and beta-hydrogen elimination.
引用
收藏
页码：5817 / 5822
页数：6
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