Tertiary C(sp <sup>3</sup> )–Si Bond Formation via Reactivity Umpolung of Silyl Reagents
A transition-metal-free decyanative silylation of malononitriles with silyl chlorides enabled by a silyl umpolung strategy is described. This reaction involves NaO<sup><i>t</i></sup>Bu-promoted silylboranes addition to malononitriles to generate electrophilic silyl cyanide and nucleophilic ketenimine intermediates in situ, which recombine to form sterically congested C(sp<sup>3</sup>)-Si bonds. This method expands silylborane reactivity and provides a general route to alkylsilanes.
Authors
- H. Huang
- Wenbo Liu (ORCID: https://orcid.org/0000-0001-5058-8672)
- Yupeng Zheng (ORCID: https://orcid.org/0000-0002-2165-7859)
- Wang Wang
Institutions
- Wuhan University (CN)
- Renmin Hospital of Wuhan University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-02-17
- DOI
- https://doi.org/10.1021/acs.orglett.6c00035
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00