Photocatalytic anti-Markovnikov addition of carboxylic acids to alkenes: an ionic mechanism under radical conditions

Photocatalytic anti-Markovnikov addition of carboxylic acids to alkenes: an ionic mechanism under radical conditions Full article

Journal

Organic Chemistry Frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2025, Volume: 12, Number: 6, Pages: 1918-1926 Pages count : 9 DOI: 10.1039/d4qo02280g

Authors

Lipilin Dmitry L. ¹ , Zubkov Mikhail O. ¹ , Kosobokov Mikhail D. ¹ , Dilman Alexander D. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation

Since the advent of photocatalysis, radical addition to alkenes has become one of the most fruitful processes for building up molecular complexity. Herein we describe a novel approach towards photocatalytic addition to alkenes, in which both new C–O and C–H bonds are formed by an ionic mechanism, rather than the conventional radical mechanism. This occurs due to two consecutive radical-polar crossover events, enabling the generation of both radical cation and carbanion species during the reaction. Such a transformation is demonstrated by the acridine-catalyzed addition of carboxylic acids to styrenes. This unique mechanism allows one to carry out the reaction in the absence of additives and also to reverse the regioselectivity of conventional ionic addition to alkenes.

Lipilin D.L. , Zubkov M.O. , Kosobokov M.D. , Dilman A.D.
Photocatalytic anti-Markovnikov addition of carboxylic acids to alkenes: an ionic mechanism under radical conditions
Organic Chemistry Frontiers. 2025. V.12. N6. P.1918-1926. DOI: 10.1039/d4qo02280g WOS Scopus OpenAlex

Web of science:	WOS:001399674600001
Scopus:	2-s2.0-86000436572
OpenAlex:	W4406311704

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