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Updated: Mar 14, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
C(sp3 )-H Functionalizations Promoted by the Gold Carbene Generated from Vinylidenecyclopropanes
De-Yao Li1, Wei Fang1, Yin Wei1
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Lu, Shanghai, 200032, China), Fax: (+86) 21-64166128.
Abstract:
The gold carbene generated from vinylidenecyclopropanes (VDCPs) can smoothly perform a C(sp3 )-H bond insertion reaction, stereoselectively affording the intramolecular C(sp3 )-H bond functionalized product, benzoxepine, with syn-configuration in moderate to good yields under mild conditions. The KIE investigation on this bond functionalization partially revealed that the carbene insertion step might be rate-determining. Using a chiral gold(I) catalyst, the first example on the asymmetric variant of gold carbene insertion into C(sp3 )-H bond has been disclosed, giving the desired products with excellent results.
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