Enantioselective C(sp(2))-H borylations of diarylmethylsilanes were catalyzed using iridium complexes with chiral pyridine-dihydroisoquinoline (PyDHIQ) ligands. High enantioselectivities (up to >99% ee) were observed for various substrates. A gram-scale synthesis was achieved using 1 mol% of the catalyst to afford a 91% yield of the desired chiral borylated organosilane product with >99% ee. (C) 2020 Elsevier Ltd. All rights reserved.