Enantioselective Electrocatalysis for the Cross‐Dehydrogenative Heteroarylation of Indoles, Pyrroles, and Furans DOI
Kang Liang, Ning Li, Minghao Liu

и другие.

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

Abstract Oxidative cross‐dehydrogenative C−H/C−H functionalizations represent an exemplary approach for synthesizing carbonyl compounds via α‐heteroarylation. Here we present the development of a direct anodic oxidative coupling process between 2‐acylimidazoles and divergent heterocyclic systems including indole, pyrrole, furan, facilitated by ferrocene‐assisted asymmetric nickel electrocatalysis with high levels enantioselectivity. Mechanistic investigations indicate that reaction initially involves formation chiral Ni‐bound α‐carbonyl radical, which is then captured heteroarene radical cation intermolecular stereoselective radical/radical coupling. The mild, scalable, robust conditions allow broad substrate scope excellent functional group tolerance, enabling access to wide range hetero‐compounds. consequential α‐heteroaromatic products can potentially be transformed into plethora synthetically valuable frameworks, as exemplified their application in total synthesis (−)‐COX‐2 inhibitor, (+)‐acremoauxin A, (+)‐pemedolac.

Язык: Английский

Enantioselective Electrocatalysis for the Cross‐Dehydrogenative Heteroarylation of Indoles, Pyrroles, and Furans DOI Open Access
Kang Liang, Ning Li, Minghao Liu

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

Abstract Oxidative cross‐dehydrogenative C−H/C−H functionalizations represent an exemplary approach for synthesizing carbonyl compounds via α‐heteroarylation. Here we present the development of a direct anodic oxidative coupling process between 2‐acylimidazoles and divergent heterocyclic systems including indole, pyrrole, furan, facilitated by ferrocene‐assisted asymmetric nickel electrocatalysis with high levels enantioselectivity. Mechanistic investigations indicate that reaction initially involves formation chiral Ni‐bound α‐carbonyl radical, which is then captured heteroarene radical cation intermolecular stereoselective radical/radical coupling. The mild, scalable, robust conditions allow broad substrate scope excellent functional group tolerance, enabling access to wide range hetero‐compounds. consequential α‐heteroaromatic products can potentially be transformed into plethora synthetically valuable frameworks, as exemplified their application in total synthesis (−)‐COX‐2 inhibitor, (+)‐acremoauxin A, (+)‐pemedolac.

Язык: Английский

Процитировано

3
Enantioselective Electrocatalysis for the Cross‐Dehydrogenative Heteroarylation of Indoles, Pyrroles, and Furans DOI
Kang Liang, Ning Li, Minghao Liu

и другие.

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

Abstract Oxidative cross‐dehydrogenative C−H/C−H functionalizations represent an exemplary approach for synthesizing carbonyl compounds via α‐heteroarylation. Here we present the development of a direct anodic oxidative coupling process between 2‐acylimidazoles and divergent heterocyclic systems including indole, pyrrole, furan, facilitated by ferrocene‐assisted asymmetric nickel electrocatalysis with high levels enantioselectivity. Mechanistic investigations indicate that reaction initially involves formation chiral Ni‐bound α‐carbonyl radical, which is then captured heteroarene radical cation intermolecular stereoselective radical/radical coupling. The mild, scalable, robust conditions allow broad substrate scope excellent functional group tolerance, enabling access to wide range hetero‐compounds. consequential α‐heteroaromatic products can potentially be transformed into plethora synthetically valuable frameworks, as exemplified their application in total synthesis (−)‐COX‐2 inhibitor, (+)‐acremoauxin A, (+)‐pemedolac.

Язык: Английский

Процитировано

0