A copper-catalyzed highly anti-selective radical
1,2-alkylarylation of terminal alkynes with aryl boronic acids and
alkyl bromides has been established. The reaction exhibits high compatibility
with a wide range of terminal alkynes and diverse aryl boronic acids,
thus providing facile access to various stereodefined trisubstituted
alkenes in high yield under mild reaction conditions. Preliminary
mechanistic investigations support the formation of alkyl radicals
and their subsequent addition to alkynes in the reaction.
A cobalt-catalyzed enantioconvergent radical Negishi C(sp 3 )−C(sp 2 ) cross-coupling of racemic benzyl chlorides with arylzinc reagents has been developed in good yield with moderate enantioselectivities. This strategy provides an expedient access toward a range of enantioenriched 1,1-diarylmethanes. Key to this discovery is the utilization of a chiral multidentate anionic N,N,Pligand to strongly coordinate with the cobalt catalyst and tune its chiral environment, thus achieving the enantiocontrol over the highly reactive prochiral alkyl radical species.
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