om501033p_si_002.cif (32.17 kB)

B(C6F5)3‑Catalyzed Synthesis of Benzofused-Siloles

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posted on 22.12.2014, 00:00 by Liam D. Curless, Michael J. Ingleson
The dehydrosilylation of 2-(SiR2H)-biphenyls catalyzed by B­(C6F5)3 and a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B­(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel–Crafts reaction facilitated by a weak base.