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Site-Selective Pyridine C-H Alkylation with Alcohols and Thiols via Single-Electron Transfer of Frustrated Lewis Pairs

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Title
Site-Selective Pyridine C-H Alkylation with Alcohols and Thiols via Single-Electron Transfer of Frustrated Lewis Pairs
Author(s)
Chang-Yin Tan; Myojeong Kim; Inyoung Park; Yuhyun Kim; Sungwoo Hong
Publication Date
2022-12
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.61, no.51
Publisher
WILEY-V C H VERLAG GMBH
Abstract
A unified strategy for the deoxygenative or desulfurative pyridylation of various alcohols and thiols has been developed through a single-electron transfer (SET) process of frustrated Lewis pairs (FLPs) derived from pyridinium salts and PtBu3. Mechanistic studies revealed that N-amidopyridinium salts serve as effective Lewis acids for the formation of FLPs with PtBu3, and the generated phosphine radical cation ionically couples with the in situ generated xanthate, eventually affording the alkyl radical through facile beta-scission under photocatalyst-free conditions. The reaction efficiency was further accelerated by visible-light irradiation. This method is conceptually appealing by using encounter complexes in FLP chemistry to promote SET, which provides a previously unrecognized opportunity for the selective heteroarylation of a diverse range of alcohols and thiols with various functional groups, even in complex settings under mild reaction conditions.
URI
https://pr.ibs.re.kr/handle/8788114/12504
DOI
10.1002/anie.202213857
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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