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Diastereoselective Homocoupling of Benzylic C(sp3)-H Bonds Enabled by Halogen Transfer
Xirong Liu1,2, Xin An1,2, Xue Zhao3
1Research & Development Institute of Northwestern Polytechnical University in Shenzhen, Shenzhen 518063, China.
Abstract:
A transition-metal- and harsh-oxidant-free strategy for diastereoselective homocoupling of benzylic α-boryl carbanions has been developed. Central to this methodology is the ability of the halogen transfer reagent to seamlessly integrate halogenation and substitution within a compatible process. Additionally, this methodology is also applicable to the homocoupling of diarylmethanes and alkylheteroarenes. Substrates bearing oxidatively sensitive functional groups were well-tolerated. Preliminary studies suggest that the hydrogen bond between two boryl groups contributes to the high diastereoselectivities.
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