Palladium-catalyzed ring-opening of cyclopropyl benzamides: synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization

被引：28

作者：

Ladd, Carolyn L. ^{[1
]}

Roman, Daniela Sustac ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Stn Downtown, Montreal, PQ H3C 3J7, Canada

来源：

TETRAHEDRON | 2013年 / 69卷 / 22期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

Cyclopropane; Palladium catalysis; C-H functionalization; Benzoazepines; Silver; C-H BONDS; INTRAMOLECULAR ALKANE ARYLATION; ENANTIOSELECTIVE SYNTHESIS; ACTIVATION; AMIDES; ACID; DERIVATIVES; OLEFINATION; SP(2); SCOPE;

D O I：

10.1016/j.tet.2013.02.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of difficult to obtain benzo[c]azepine-1-ones are synthesized via a novel palladium-catalyzed, silver-promoted intramolecular cyclization of cyclopropyl benzamides. This biologically important class of molecules is prepared in an efficient and high-yielding manner from easily accessible starting materials. Both aryl bromides and iodides are effective substrates for the transformation. Mechanistic studies indicate that the reaction proceeds through a cyclopropyl C(sp(3))-H cleavage step, followed by ring-opening, deprotonation, and reductive elimination. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4479 / 4487

页数：9

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