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February 19, 2026Organic Letters0 citations

Tertiary C(sp 3 )–Si Bond Formation via Reactivity Umpolung of Silyl Reagents

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YZYupeng ZhengWWWang WangHHH. Huang

Key Points

  • This research aims to explore a new method for forming C(sp3)-Si bonds through silyl umpolung.
  • Employs a transition-metal-free decyanative silylation approach.
  • Utilizes NaOtBu to promote the addition of silylboranes to malononitriles.
  • Generates intermediates including electrophilic silyl cyanide and nucleophilic ketenimine.
  • Successful formation of sterically congested C(sp3)-Si bonds.
  • Demonstrated expansion of silylborane reactivity.
  • Provided a general synthetic route to alkylsilanes.

Abstract

A transition-metal-free decyanative silylation of malononitriles with silyl chlorides enabled by a silyl umpolung strategy is described. This reaction involves NaOtBu-promoted silylboranes addition to malononitriles to generate electrophilic silyl cyanide and nucleophilic ketenimine intermediates in situ, which recombine to form sterically congested C(sp3)-Si bonds. This method expands silylborane reactivity and provides a general route to alkylsilanes.

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Cite This Study

Zheng et al. (2026) studied this question.

synapsesocial.com/papers/6996a8efecb39a600b3f0261https://doi.org/10.1021/acs.orglett.6c00035
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