Controllable Si–C Bond Formation from Trihydrosilanes En Route to Synthesis of 1,4-Azasilinanes with Diverse Silyl Functionalities

Abstract

A B­(C6F5)3-catalyzed controllable inter/intra-/intermolecular Si–C bond formation process has been developed from trihydrosilane and dienamide with alkenes, anilines, or aryl iodides. A variety of 1,4-azasilinanes have been generated with diverse exo-cyclic heteroleptic disubstitutions on silicon, thereby expanding the range of silaazacyclic rings available for the discovery of silicon-containing drugs.

Nascent developments in main group element-catalyzed hydrosilylation and dehydrogenative silylation of alkenes and alkynes

“…Song and co-workers reported the synthesis of 1,4-azasilinanes through 38 catalyzed intra- and intermolecular Si–C bond formation from trihydrosilane and dienamide with alkenes, anilines or aryl iodides (Scheme 40). 110 Through this strategy, 1,4-azasilinanes were generated with a series of exo -cyclic heteroleptic disubstitutions on silicon. The authors utilized this protocol for late-stage functionalization of drug analogues such as salicylic esters and estrone in 96 and 75% yield, respectively.…”

“…The authors utilized this protocol for late-stage functionalization of drug analogues such as salicylic esters and estrone in 96 and 75% yield, respectively. 110…”