Tetrahedron

Palladium-catalyzed ring-opening of cyclopropyl benzamides: synthesis of benzo [c] azepine-1-ones via C (sp 3)–H functionalization

CL Ladd, DS Roman, AB Charette

Index: Ladd, Carolyn L.; Roman, Daniela Sustac; Charette, Andre B. Tetrahedron, 2013 , vol. 69, # 22 p. 4479 - 4487

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Citation Number: 16

Abstract

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 ...