Flavin/I2‐Catalyzed Aerobic Oxidative C–H Sulfenylation of Aryl‐Fused Cyclic Amines

We report an aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols catalyzed by flavin/I2 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 posit...

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Published inEuropean journal of organic chemistry Vol. 2020; no. 25; pp. 3889 - 3895
Main Authors Jiang, Xinpeng, Zhao, Zongchen, Shen, Zhifeng, Chen, Keda, Fang, Liyun, Yu, Chuanming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.07.2020
Wiley Subscription Services, Inc
Subjects
Amines
Aromatic compounds
Chemistry
Chemistry, Organic
Heterocyclic compounds
Indoles
Nitrogen heterocycles
Oxidation
Oxidizing agents
Physical Sciences
Science & Technology
Sulfenylation
Synthetic methods
Thiols
NITROGEN-HETEROCYCLES
Sulfenylation
TUBULIN POLYMERIZATION
CATALYZED REGIOSELECTIVE SULFENYLATION
POTENT INHIBITORS
EFFICIENT CATALYST
ELECTRON-TRANSFER
Nitrogen heterocycles
ACCEPTORLESS DEHYDROGENATION
BIOLOGICAL EVALUATION
Oxidation
Synthetic methods
Indoles
METAL-FREE
N-HETEROCYCLES
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Abstract We report an aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols catalyzed by flavin/I2 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. A metal‐free aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols was developed with excellent functional compatibility. While flavin I catalyzed the C–H sulfenylation of indolines to afford 3‐sulfenylindoles, flavin II enabled transformations resulting in substitution at the position para to the N atom on the aryl ring to obtain 6‐sulfenylquinolines.
AbstractList We report an aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols catalyzed by flavin/I2 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.
We report an aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols catalyzed by flavin/I2 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. A metal‐free aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols was developed with excellent functional compatibility. While flavin I catalyzed the C–H sulfenylation of indolines to afford 3‐sulfenylindoles, flavin II enabled transformations resulting in substitution at the position para to the N atom on the aryl ring to obtain 6‐sulfenylquinolines.
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.
Author Shen, Zhifeng
Zhao, Zongchen
Jiang, Xinpeng
Chen, Keda
Yu, Chuanming
Fang, Liyun
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Issue 25
Keywords NITROGEN-HETEROCYCLES
Sulfenylation
TUBULIN POLYMERIZATION
CATALYZED REGIOSELECTIVE SULFENYLATION
POTENT INHIBITORS
EFFICIENT CATALYST
ELECTRON-TRANSFER
Nitrogen heterocycles
ACCEPTORLESS DEHYDROGENATION
BIOLOGICAL EVALUATION
Oxidation
Synthetic methods
Indoles
METAL-FREE
N-HETEROCYCLES
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Snippet We report an aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols catalyzed by flavin/I2 for the first time. While flavin I...
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...
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wiley
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SubjectTerms Amines
Aromatic compounds
Chemistry
Chemistry, Organic
Heterocyclic compounds
Indoles
Nitrogen heterocycles
Oxidation
Oxidizing agents
Physical Sciences
Science & Technology
Sulfenylation
Synthetic methods
Thiols
Title Flavin/I2‐Catalyzed Aerobic Oxidative C–H Sulfenylation of Aryl‐Fused Cyclic Amines
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.202000508
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https://www.proquest.com/docview/2420532542/abstract/
Volume 2020
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