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

Shi, Yufeng and Shi, Xiaonan and Zhang, Jinyu and Qin, Ying and Li, Bo and Zhao, Dongbing (2022) Sila-spirocyclization involving unstrained C(sp³)-Si bond cleavage. Nature Communications, 13 . Art. No. 6697. ISSN 2041-1723. PMCID PMC9637223. doi:10.1038/s41467-022-34466-4. https://resolver.caltech.edu/CaltechAUTHORS:20221208-575982500.6

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1038/s41467-022-34466-4DOIArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/pmc9637223/PubMed CentralArticle
ORCID:
AuthorORCID
Li, Bo0000-0002-8019-8891
Zhao, Dongbing0000-0003-2583-1575
Alternate Title:Sila-spirocyclization involving unstrained C(sp3)−Si bond cleavage
Additional Information:We are grateful for the financial support from the National Natural Science Foundation of China (22071114, 22022103, 21871146), Haihe Laboratory of Sustainable Chemical Transformations, the National Key Research and Development Program of China (2019YFA0210500), the “Frontiers Science Center for New Organic Matter”, Nankai University (Grant Number 63181206), and the Fundamental Research Funds for the Central Universities and Nankai University.
Funders:
Funding AgencyGrant Number
National Natural Science Foundation of China22071114
National Natural Science Foundation of China22022103
National Natural Science Foundation of China21871146
Haihe Laboratory of Sustainable Chemical TransformationsUNSPECIFIED
National Key Research and Development Program of China2019YFA0210500
Nankai University63181206
Fundamental Research Funds for the Central UniversitiesUNSPECIFIED
PubMed Central ID:PMC9637223
DOI:10.1038/s41467-022-34466-4
Record Number:CaltechAUTHORS:20221208-575982500.6
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20221208-575982500.6
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:118275
Collection:CaltechAUTHORS
Deposited By: Research Services Depository
Deposited On:11 Jan 2023 15:47
Last Modified:17 Jan 2023 18:43

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