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.
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.Additional details
- Alternative title
- Sila-spirocyclization involving unstrained C(sp3)−Si bond cleavage
- PMCID
- PMC9637223
- Eprint ID
- 118275
- Resolver ID
- CaltechAUTHORS:20221208-575982500.6
- 22071114
- National Natural Science Foundation of China
- 22022103
- National Natural Science Foundation of China
- 21871146
- National Natural Science Foundation of China
- Haihe Laboratory of Sustainable Chemical Transformations
- 2019YFA0210500
- National Key Research and Development Program of China
- 63181206
- Nankai University
- Fundamental Research Funds for the Central Universities
- Created
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2023-01-11Created from EPrint's datestamp field
- Updated
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2023-01-17Created from EPrint's last_modified field