Pd-Catalyzed Skeletal Remodeling of Bicyclo[1.1.0]butane Carboxamides to Azabicyclo[3.1.0]hexan-2-ones via a Pd(II)–Carbene Intermediate

Abstract

We report the efficient and versatile Pd-catalyzed skeletal remodeling of bicyclo[1.1.0]butane carboxamides to azabicyclo[3.1.0]hexan-2-ones via an in situ-generated transient and highly reactive Pd(II)–carbene intermediate. This transformation enabled access to functionalized allyl-tethered 3-azabicyclo[3.1.0]hexan-2-one scaffolds via skeletal remodeling. The excellent tolerance of the reaction to functional groups across structurally and electronically diverse substrates demonstrates their broad applicability. The operational simplicity and practical utility of this protocol scale to gram-scale synthesis of azabicyclo[3.1.0]hexan-2-ones as well as to synthetic utility and late-stage structural modifications.