Palladium-catalyzed three-component coupling reactions of 2-(cyanomethyl)phenol, aryl halides, and carbon monoxide

被引：10
作者：
Murai, Masahito [1 ]
Okamoto, Kazuhiro [1 ]
Miki, Koji [1 ]
Ohe, Kouichi [1 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan
来源：
TETRAHEDRON | 2015年 / 71卷 / 26-27期
关键词：
Tandem catalysis; Carbonylation; Cycloisomerization; 3-Acyl-2-aminobenzofuran; CYCLIZATION; CARBOPALLADATION; NITRILES; ALKYNES; IDENTIFICATION; CARBONYLATION; CONSTRUCTION; ANNULATION; COMPLEXES; ESTERS;
D O I：
10.1016/j.tet.2015.04.049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three-component coupling reactions of 2-(cyanomethyl)phenol, aryl halides, and carbon monoxide (CO) in orthogonal-tandem catalysis were investigated. In the reactions, 2-(cyanomethyl)phenyl esters, which are produced through Pd(PPh3)(4)-catalyzed alkoxycarbonylation of aryl halides with 2-(cyano-methyl)phenol, undergo cycloisomerization in situ catalyzed by Pd(PCy3)(2) as a co-catalyst to give 3-acyl-2-aminobenzofurans. Palladium species with homoleptic tertiary phosphines, such as Pd(PPh3)(4) and Pd(PCy3)(2), can catalyze the mechanistically distinct reactions in an orthogonal tandem manner without interference. By switching the base used in this reaction, 3-acyl-2-(N-acylamino)benzofurans were obtained as major products instead of 3-acyl-2-aminobenzofurans. Given that 2-(cyanomethyl)phenols can be synthesized from commercially available salicylic acid derivatives in two steps, the present method thus provides facile access to synthetically useful 3-acyl-2-aminobenzofurans. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4432 / 4437
页数：6
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