Carbenes containing boron as one or both substituents at the divalent carbon are rare. In this work, we describe the synthesis of a new indan-based precursor 1 to the chloroborylcarbene 2. The ability of 1 to release 2 upon photolysis, and the subsequent reaction of 2 to undergo cycloaddition to alkenes to form 3 and hydrogen abstraction to produce 4, are described. Results of computational studies using density functional theory and coupled-cluster methods to understand the structure and behavior of 2 are presented. Finally, the possibility of further structural elaboration of 1 by metal-catalyzed coupling reactions to yield precursors to other interesting carbenes are discussed.

Photochemical generation of a borylcarbene from an indan-based precursor

ACS Spring 2022

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