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. 2026 Feb 27.
doi: 10.1038/s41467-026-69513-x. Online ahead of print.

Ketone displacement and migration enabled by trifunctionalization of vinyl triflates

Shiyang Wang  1   2 , Tong Yao  1   2 , Yu Liu  3 , Yangyang Li  4 , Guoyin Yin  5
Affiliations

Ketone displacement and migration enabled by trifunctionalization of vinyl triflates

Shiyang Wang et al. Nat Commun. .

Abstract

Functional group displacement and migration represent powerful, yet underexplored strategies in synthetic chemistry, offering unique opportunities for molecular diversification and drug discovery. Here, we report a nickel-catalyzed deoxygenative trifunctionalization of vinyl triflates, which enables the efficient synthesis of structurally diverse, boron-containing polysubstituted cyclohexanes featuring quaternary carbon centers. This reaction is a key step enabling aryl displacement of a ketone group and its migration to an adjacent carbon center. Notably, the transformation exhibits broad substrate scope and exceptional, programmable diastereoselectivity in arylative ketone migration. Moreover, this transformation enables efficient α-arylation of unsymmetrical ketones with excellent regio- and diastereoselective control-an outcome that remains challenging to achieve using existing methods. Furthermore, this strategy is particularly well-suited for the late-stage functionalization of structurally complex bioactive molecules, facilitating the rapid generation of analogs.

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Conflict of interest statement

Competing interests: Authors declare no competing interests.

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