Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds.

J Org Chem

State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing 100029, China.

Published: September 2024

Dihydroaurones, which are derivatives of aurones, exhibit similar biological activity. Although there are many synthetic methods for dihydroaurones, ecofriendly methodologies that circumvent the use of precious metals still need to be explored. In this work, a catalyst-free, visible-light-driven synthesis of dihydroaurones has been developed through the cyclization of aromatic diazo compounds. The reaction proceeded smoothly under mild conditions, resulting in a series of dihydroaurones in moderate to high yields. Mechanistic investigation suggests that this process involves a radical-pair Stevens rearrangement.

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http://dx.doi.org/10.1021/acs.joc.4c01064DOI Listing

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