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Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids
Sudheesh T Sivanandan1, Benjamin Owen2, Patrick J Guiry2
1School of Chemistry, University of Nottingham, Nottingham NG7 2RD, U.K.
Abstract:
Bismacycles featuring a sulfone-bridged scaffold have recently been developed as versatile and convenient electrophilic arylating agents. Here, we report that the exocyclic aryl group, which is ultimately transferred to a nucleophilic coupling partner, can be functionalized through cross-coupling, heteroatom substitutions, oxidations and reductions, and protecting group manipulations. This "postsynthetic modification" approach provides concise and divergent access to complex aryl bismacycles. The utility of the functionalized bismacycles in electrophilic arylation of C-H and O-H bonds is demonstrated.
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