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Sila-spirocyclization involving unstrained C(sp³)-Si bond cleavage.

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.

SUBMITTER: Shi Y

PROVIDER: S-EPMC9637223 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Sila-spirocyclization involving unstrained C(sp3)-Si bond cleavage.

Shi Yufeng Y Shi Xiaonan X Zhang Jinyu J Qin Ying Y Li Bo B Zhao Dongbing D

Nature communications 20221105 1

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</sup ...[more]

PMID: 36335183

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Author Correction: Sila-spirocyclization involving unstrained C(sp3)-Si bond cleavage.

Project description: Not available

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