Synthesis of gem-diboromethyl substituted bicyclo[1.1.1]pentanes and their application in palladium-catalysed cross couplings

01 November 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


We describe a general transition-metal free synthesis of gem-diboromethyl substituted bicyclo[1.1.1]pentane (BCP) and other related C(sp3)-rich carbocyclic benzene bioisosteres from their corresponding p-tosylhydrazones. These novel functionalized benzene bioisosteres demonstrated unique reactivities towards palladium-catalyzed C(sp2)-C(sp3) cross couplings. The overall transformation can be applied to relatively complex substrates with potential utility in drug discovery.


Cross coupling


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