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<p>The ubiquity of <i>N</i>-heterocyclic carbenes (NHCs) in diverse areas of chemical research typically arises from their potent stabilising capabilities and role as innocent spectators to stabilise otherwise non-bottleable compounds and complexes. This has, until now, been particularly true for NHC-stabilised stannylenes, with no exceptions reported thus far. Herein, we demonstrate that the combination of heteroleptic terphenyl-/amido-based stannylenes and tetra-alkyl substituted NHCs renders the corresponding NHC-ligated stannylenes highly reactive, yet isolable. In solution, this induces sterically controlled inter- and intramolecular C(sp<sup>3</sup>)–H bond scissions, resulting in the selective formation of stannylene metallocycles that depend on both the NHC source and the <i>meta</i>-terphenyl ligand coordinated to tin.</p>

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Carbene-activated stannylenes to access selective C(sp3)–H bond scission at the steric limit

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年3月18日

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  • Jennifer Klaucke,
  • Navutheya Sinthathurai,
  • Christopher Golz,
  • Oliver P. E. Townrow,
  • Malte Fischer

摘要

The ubiquity of N-heterocyclic carbenes (NHCs) in diverse areas of chemical research typically arises from their potent stabilising capabilities and role as innocent spectators to stabilise otherwise non-bottleable compounds and complexes. This has, until now, been particularly true for NHC-stabilised stannylenes, with no exceptions reported thus far. Herein, we demonstrate that the combination of heteroleptic terphenyl-/amido-based stannylenes and tetra-alkyl substituted NHCs renders the corresponding NHC-ligated stannylenes highly reactive, yet isolable. In solution, this induces sterically controlled inter- and intramolecular C(sp3)–H bond scissions, resulting in the selective formation of stannylene metallocycles that depend on both the NHC source and the meta-terphenyl ligand coordinated to tin.