Photo-induced copper-catalyzed sequential 1,n-HAT enabling the formation of cyclobutanols

Zhusong Cao, Jianye Li and Guozhu Zhang ()
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Zhusong Cao: Central China Normal University (CCNU)
Jianye Li: Central China Normal University (CCNU)
Guozhu Zhang: Central China Normal University (CCNU)

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Cyclobutanols are privileged cyclic skeletons in natural products and synthetic building blocks. C(sp3)−H functionalization is a prolonged challenge in organic synthesis. The synthesis of cyclobutanols through double C(sp3)-H bond functionalization remains elusive. Here we report the efficient synthesis of cyclobutanols through intermolecular radical [3 + 1] cascade cyclization, involving the functionalization of two C − H bonds through sequential hydrogen atom transfer. The copper complex reduces the iodomethylsilyl alcohols efficiently under blue-light irradiation to initiate the tandem transformation. The mild reaction tolerates a broad range of functional groups and allows for the facile generation of elaborate polycyclic structures.

Date: 2021
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DOI: 10.1038/s41467-021-26670-5

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