Visible-Light-Promoted Radical Markovnikov Bromohydroxylation of Alkenes With Molecular Oxygen and Dioxane as Hydroxyl Source

Zeng, Zude and Liang, Wenxu and Mei, Haibo and Escorihuela, Jorge and Kiss, Loránd and Han, Jianlin (2026) Visible-Light-Promoted Radical Markovnikov Bromohydroxylation of Alkenes With Molecular Oxygen and Dioxane as Hydroxyl Source. Advanced Synthesis and Catalysis, 386 (9). No. e70439. ISSN 1615-4150

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Abstract

A visible-light-promoted radical bromohydroxylation reaction of quinazolinone-tethered alkenes with CBr4 as a bromine source has been developed, which affords vicinal bromohydrins as products in up to 66% yields. This work represents the first example of employing molecular oxygen and dioxane as hydroxyl source in bromohydroxylation reaction of alkenes. Control experiments and DFT calculations disclose that the reaction proceeds via a Markovnikov regioselectivity. This reaction features mild conditions and scale-up applicability, which represents a new bromohydroxylation reaction mode and also provides an easy and green access to vicinal bromohydrins.

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