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- Title
Sila-spirocyclization involving unstrained C(sp<sup>3</sup>)−Si bond cleavage.
- Authors
Shi, Yufeng; Shi, Xiaonan; Zhang, Jinyu; Qin, Ying; Li, Bo; Zhao, Dongbing
- Abstract
C − Si Bond cleavage is one of the key elemental steps for a wide variety of silicon-based transformations. However, the cleavage of unstrained Si−C(sp3) bonds catalyzed by transition metal are still in their infancy. They generally involve the insertion of a M − C(sp2) species into the C − Si bond and consequent intramolecular C(sp2)‒Si coupling to exclusively produce siloles. Here we report the Pd-catalyzed sila-spirocyclization, in which the Si−C(sp3) bond is activated by the insertion of a M − C(sp3) species and followed by the formation of a new C(sp3)‒Si bond, allowing the construction of diverse spirosilacycles. This reactivity mode, which is strongly supported by DFT calculations may open an avenue for the Si−C(sp3) bond cleavage and silacycle synthesis. Methods that enable the cleavage of Si−C(sp3) bonds catalytically remain rare. Here the authors report the synthesis of spirosilacycles via palladium-catalysed spiro-sila-cyclization of trialkylsilane derivatives; the reaction proceeds via cleavage of a C(sp3)−Si bond and insertion of an alkylpalladium complex.
- Subjects
TRANSITION metals; SILOLES
- Publication
Nature Communications, 2022, Vol 13, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-022-34466-4