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Site-Selective Direct C-H Pyridylation of Unactivated Alkanes by Triplet Excited Anthraquinone

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Title
Site-Selective Direct C-H Pyridylation of Unactivated Alkanes by Triplet Excited Anthraquinone
Author(s)
Wooseok Lee; Sungwoo Jung; Minseok Kim; Sungwoo Hong
Publication Date
2021-02
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.143, no.7, pp.3003 - 3012
Publisher
AMER CHEMICAL SOC
Abstract
Site-selective C-H functionalization in chemical feedstocks is a challenging and useful reaction in the broad field of chemical research. Here, we report a modular photochemical platform for the site-selective C-H pyridylation of unactivated hydrocarbons via the unique synergistic effects of triplet excited anthraquinone and an amidyl radical-based reverse hydrogen atom transfer (RHAT) agent. The selective pyridylation of tertiary and secondary C(sp(3))-H bonds in abundant chemical feedstocks was achieved by employing various N-aminopyridinium salts in a highly selective fashion, thus providing a new catalytic system for the direct construction of high-value-added compounds under ambient reaction conditions. Moreover, this operationally simple protocol is applicable to a variety of linear-, branched-, and cyclo-alkanes and more complex molecules with high degrees of site selectivity under visible-light conditions, which provides rapid and straightforward access to versatile synthons for upgrading feedstocks under mild, metal-free reaction conditions.
URI
https://pr.ibs.re.kr/handle/8788114/9323
DOI
10.1021/jacs.1c00549
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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