Ring-opening silylation of -arylindoles endocyclic C-N bond cleavage triggered by silylboranes

The cleavage of heteroaromatic endocyclic carbon-heteroatom bonds to assemble C-Si bonds is scarce. Here, we demonstrate an unprecedented dearomatization silylation of N -arylindoles arising from reductive activation initiated by electron-rich silylboronic complexes to deliver silyl styrenes with pe...

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Published in:Chemical communications (Cambridge, England) England), 2024-10, Vol.6 (83), p.1198-11983
Main Authors: Tian, Ye, Sun, Hanying, Cui, Benqiang, Han, Shaoyue, Wang, Tianle, Shi, Yanhui, Cao, Changsheng
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Summary:The cleavage of heteroaromatic endocyclic carbon-heteroatom bonds to assemble C-Si bonds is scarce. Here, we demonstrate an unprecedented dearomatization silylation of N -arylindoles arising from reductive activation initiated by electron-rich silylboronic complexes to deliver silyl styrenes with perfect stereoselectivity. Ring-opening silylation of indoles via reductive activation triggered by electron-rich silylboronic complexes has been successfully developed to produce silyl styrenes with perfect stereoselectivity.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc02998d