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

Yufeng Shi, Xiaonan Shi, Jinyu Zhang, Ying Qin, Bo Li () and Dongbing Zhao ()
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Yufeng Shi: Nankai University
Xiaonan Shi: Nankai University
Jinyu Zhang: Nankai University
Ying Qin: Nankai University
Bo Li: California Institute of Technology
Dongbing Zhao: Nankai University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-34466-4

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