Iridium-catalyzed diborylation of benzylic C–H bonds directed by a hydrosilyl group: synthesis of 1,1-benzyldiboronate esters†
We describe a regioselective diborylation of primary benzylic C–H bonds catalyzed by [Ir(COD)OMe]2 and 4,4′-di-tert-butyl-2,2′-bipyridine (dtbpy). The hydrosilyl group acts as a traceless directing group, providing access to a range of 1,1-benzyldiboronate esters in good yields. Transformations of the 1,1-benzyldiboronate ester products include chemoselective Suzuki–Miyaura cross-couplings and synthesis of tetrasubstituted alkenyl boronate esters.
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