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Borane-catalyzed reductive silylalkylation and silylalkenylation of N-heteroarenes with alkenes/alkynes
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DOI：10.1007/s11426-026-3540-7.png)
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Abstract
En 中文
The precise transformation of reductive intermediates derived from N-heteroarenes represents a promising yet challenging strategy for the versatile synthesis of cyclic amines. Herein, we report the first reductive silylalkylation and silylalkenylation of N-heteroarenes, enabled by unsaturated C–C bonds as connectivities and B(C6F5)3/silane as an efficient catalytic system. This method offers several notable advantages, including readily available feedstocks, high selectivity, and good step economy. These features underscore the practicality of this approach for the direct reductive functionalization of N-heteroarenes in a regioselective manner. Mechanistic studies indicate that the reaction proceeds via borane-induced activation of unsaturated C–C double or triple bonds to generate carbocations, reductive hydrosilylation of N-heteroarenes, and selective C6 electrophilic substitution of the reduced N-heteroarene intermediates with the carbocation species. In this work, the strategy of using borane-induced silylium ions to trap electron-rich intermediates in situ is expected to open new avenues for the development of novel tandem reactions.
Keywords:
N-heteroarenes
reductive silylalkylation and silylalkenylation
borane catalysis
silylium ions
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