Photocatalytic Markovnikov-type addition and cyclization of terminal alkynes leading to 4-sulfonyl quinoline-2(1)-ones

A new and expedient photocatalytic protocol for the construction of quinolin-2(1 H )-ones via Markovnikov-type sulfonylation/6-endo-trig cyclization/selective C(O)-CF 3 bond cleavage starting from N -alkyl- N -(2-ethynylphenyl)-2,2,2-trifluoroacetamides and sulfinic acids has been developed. It is a...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 33; pp. 5112 - 5115
Main Authors Zhai, Yu-Lin, Zhou, Hui, Liu, Qing-Quan, Leng, Bo-Rong, Zhang, Zixian, Li, Jia-Zhuo, Wang, De-Cai, Zhu, Yi-Long
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 21.04.2022
Subjects
Alkynes
Alkynes - chemistry
Cyclization
Molecular Structure
Photocatalysis
Quinoline
Quinolines
Substrates
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Summary:A new and expedient photocatalytic protocol for the construction of quinolin-2(1 H )-ones via Markovnikov-type sulfonylation/6-endo-trig cyclization/selective C(O)-CF 3 bond cleavage starting from N -alkyl- N -(2-ethynylphenyl)-2,2,2-trifluoroacetamides and sulfinic acids has been developed. It is as an unprecedented protocol for the preparation of 4-sulfonylquinoline-2(1 H )-ones with high efficiency, mild reaction conditions, acceptable yields and a wide range of substrates. A novel and convenient photocatalytic cyclization of terminal alkynes for the construction of 4-sulfonylquinoline-2(1 H )-ones by radical Markovnikov addition/6-endo-trig cyclization/selective C(O)-CF 3 bond cleavage was disclosed.
Bibliography:2145528
For ESI and crystallographic data in CIF or other electronic format see DOI
Electronic supplementary information (ESI) available: For ESI and crystallographic data in CIF or other electronic format. CCDC
10.1039/d2cc01169g
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01169g