Through mechanism-based and data-driven synergistic reaction design, we discovered a novel base-mediated C−B bond activation mechanism of benzylic boronates. This methodology was applied to the rapid construction of β-silyl (or boryl) 1,1-diarylalkanes, exploring the compatibility of over 10,000 substrate combinations.

DOI: 10.1039/D3SC03666A

By shifting the chemical equilibrium of the benzylic boronate-base complex to the free carbanion state, we developed a general, practical, and simple method for the construction of β-silyl/boryl functionalized 1,1-diarylalkanes.