Photo-induced copper-catalyzed sequential 1,n-HAT enabling the formation of cyclobutanols.
basic_science · Level V
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- Record sourced from PubMed, PMID 34737326.
- Also identified by DOI 10.1038/s41467-021-26670-5 and PMC identifier 8569169.
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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.