Selective C(sp3)-C(sp3) reduction and metathesis of ketones

Abstract

The C–C bond reduction and metathesis are fundamentally important in organic synthesis. However, homogeneously reducible C–C bonds are currently limited to either strained rings or to specific and prefunctionalized sites; and there are no practical methods for tandem C–C reduction and intramolecular C(sp3)–C(sp3) metathesis. Here we report a versatile approach for selective reduction of unstrained C(sp3)–C(sp3) bond of ketones, including hydrogenolytic retro-[2+2+2]-cycloreversion of 2,4-diaroylcyclohexanols, without requiring protecting groups. We have also established an unprecedented intramolecular C(sp3)–C(sp3) metathesis, thus enabling the cyclizative degradation of poly(vinylketone). The present C–C cleavage occurs via a bimetallic pathway and nucleophile trapping of resulting enone is crucial for C–C cleavage relay. These results would open new prospect for deconstruction of organic molecules.

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