Carbene-Mediated Access to Bicyclo[1.1.1]pentanes

Keywords

photoredox catalysis - carbene chemistry - bicyclo[1.1.0]butanes - bicyclo[1.1.0]pentanes

Significance

This study develops an efficient method to access 2-substituted bicyclo[1.1.1]pentanes, which are valuable benzene bioisosteres in drug discovery. A concise one-pot sequence is described where bicyclo[1.1.0]butanes (BCBs) are initially formed using a dirhodium-catalyzed cyclopropanation, followed by visible-light triplet carbene insertion. Supported by computational studies, the method provides practical yields and broadens synthetic tools for medicinal chemistry.

Comment

This work offers a clear mechanistic insight into triplet carbene insertion, with computational studies elucidating a favored pathway and preferred selectivity. This one-pot strategy circumvents unstable intermediates, achieving yields of up to 77 %. The demonstrated aryl stabilization and excited-state control provide key tools that may be useful for designing future photoinduced carbene processes.

Publication History

Article published online:
30 October 2025