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Photocatalytic Decarboxylative Pyridylation of Carboxylic Acids Using In Situ-Generated Amidyl Radicals as Oxidants

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Title
Photocatalytic Decarboxylative Pyridylation of Carboxylic Acids Using In Situ-Generated Amidyl Radicals as Oxidants
Author(s)
Changha Kim; Jinwook Jeong; Mari Vellakkaran; Sungwoo Hong
Publication Date
2022-11
Journal
ACS CATALYSIS, v.12, no.21, pp.13225 - 13233
Publisher
AMER CHEMICAL SOC
Abstract
Site-selective C-H functionalization of heteroarenes is important for the rapid modification of bioactive molecules. Herein, we report an efficient photocatalytic platform for the visible-light-mediated C-H alkylation of pyridines at the C4 position using alkyl carboxylic acids as alkylating agents under external oxidant-free conditions. Importantly, the released N-centered radical can serve as an effective oxidizing agent for single-electron transfer (SET) oxidation to efficiently regenerate the photocatalyst. This photocatalytic system is appealing from a mechanistic perspective and is amenable to a broad substrate scope for carboxylic acids and pyridines containing oxidatively sensitive functionalities that do not hold up to other procedures. The strategy offers a practical approach for the C4-selective pyridylation of a diverse range of primary, secondary, and tertiary carboxylic acids and amino acids with various functional groups under mild, metal-free conditions.
URI
https://pr.ibs.re.kr/handle/8788114/12571
DOI
10.1021/acscatal.2c04417
ISSN
2155-5435
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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