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Flavin/I 2 ‐Catalyzed Aerobic Oxidative C–H Sulfenylation of Aryl‐Fused Cyclic Amines
Author(s) -
Jiang Xinpeng,
Zhao Zongchen,
Shen Zhifeng,
Chen Keda,
Fang Liyun,
Yu Chuanming
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000508
Subject(s) - chemistry , flavin group , aryl , catalysis , oxidative phosphorylation , combinatorial chemistry , oxidative coupling of methane , photochemistry , medicinal chemistry , organic chemistry , biochemistry , alkyl , enzyme
We report an aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols catalyzed by flavin/I 2 for the first time. While flavin I catalyzed the C–H sulfenylation of indolines to afford 3‐sulfenylindoles, flavin II enabled transformations resulted in substitution at the position para to the N atom on the aryl ring to obtain 6‐sulfenylquinolines. The advantages of this metal‐free oxidative C–S coupling approach utilizing ambient oxygen as the terminal oxidant were that it was conducted under mild conditions with good atom‐efficiency and excellent functional compatibility.