Photochemical rearrangement of isonitriles via energy transfer catalysis

Qi-Xin Dong, Yi-Hong Ke, Yi-Hui Tang, Song Yu and Huan-Ming Huang ()
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Qi-Xin Dong: ShanghaiTech University
Yi-Hong Ke: ShanghaiTech University
Yi-Hui Tang: ShanghaiTech University
Song Yu: The University of Manchester
Huan-Ming Huang: ShanghaiTech University

Nature Communications, 2025, vol. 16, issue 1, 1-10

Abstract: Abstract Functional group interconversion, a pivotal synthetic technique for precise editing of molecular building blocks, is particularly rare when facilitated by energy transfer catalysis. Herein, we showcase two instances of photochemical rearrangement of isonitriles, facilitated by energy transfer catalysis under visible light. The di-π-ethane rearrangement and di-π-propane rearrangement proceed through a six-membered transition state, offering a fresh synthetic paradigm for constructing three- and five-membered molecular architectures. Notably, these open-shell rearrangements demonstrate a vast substrate scope, compatibility with diverse functional groups, and applicability to complex drug and natural product derivatives, thereby presenting a complementary strategy for advancing energy transfer-enabled functional group interconversion. Furthermore, the photochemical rearrangements of isonitriles have been supported by computational studies.

Date: 2025
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DOI: 10.1038/s41467-025-64460-5

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