Visible-Light Induced Oxidative Annulation of Enamides to 2,4,5-Trisubstituted Oxazole Skeletons

Dan Ning Wang; Qi Lin; Xun Wang; Keyuan Zhang; Xin Hua Duan; Le Liu

doi:10.1002/ajoc.202300019

Visible-Light Induced Oxidative Annulation of Enamides to 2,4,5-Trisubstituted Oxazole Skeletons

Dan Ning Wang
, Qi Lin
, Xun Wang
, Keyuan Zhang
, Xin Hua Duan
, Le Liu

School of Chemistry

Xi'an Jiaotong University

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

A novel approach to various trisubstituted oxazoles (28 examples, up to 88% yield) has been developed via 9H-thioxanthen-9-one (TX) mediated oxidative annulation of N-acetyl enamide under visible light irradiation in the presence of BF₃ ⋅ Et₂O (2.0 equiv) and 40 mol% of PhNO₂. This metal-free procedure features high atom and step economy, green and mild conditions and broad substrate scope.

Original language	English
Article number	e202300019
Journal	Asian Journal of Organic Chemistry
Volume	12
Issue number	5
DOIs	https://doi.org/10.1002/ajoc.202300019
State	Published - May 2023

Keywords

Enamides
Hydrogen atom Transfer
Oxazoles
Oxidative annulation
Photocatalysis

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10.1002/ajoc.202300019

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title = "Visible-Light Induced Oxidative Annulation of Enamides to 2,4,5-Trisubstituted Oxazole Skeletons",

abstract = "A novel approach to various trisubstituted oxazoles (28 examples, up to 88\% yield) has been developed via 9H-thioxanthen-9-one (TX) mediated oxidative annulation of N-acetyl enamide under visible light irradiation in the presence of BF3 ⋅ Et2O (2.0 equiv) and 40 mol\% of PhNO2. This metal-free procedure features high atom and step economy, green and mild conditions and broad substrate scope.",

keywords = "Enamides, Hydrogen atom Transfer, Oxazoles, Oxidative annulation, Photocatalysis",

author = "Wang, \{Dan Ning\} and Qi Lin and Xun Wang and Keyuan Zhang and Duan, \{Xin Hua\} and Le Liu",

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doi = "10.1002/ajoc.202300019",

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volume = "12",

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T1 - Visible-Light Induced Oxidative Annulation of Enamides to 2,4,5-Trisubstituted Oxazole Skeletons

AU - Wang, Dan Ning

AU - Lin, Qi

AU - Wang, Xun

AU - Zhang, Keyuan

AU - Duan, Xin Hua

AU - Liu, Le

PY - 2023/5

Y1 - 2023/5

N2 - A novel approach to various trisubstituted oxazoles (28 examples, up to 88% yield) has been developed via 9H-thioxanthen-9-one (TX) mediated oxidative annulation of N-acetyl enamide under visible light irradiation in the presence of BF3 ⋅ Et2O (2.0 equiv) and 40 mol% of PhNO2. This metal-free procedure features high atom and step economy, green and mild conditions and broad substrate scope.

AB - A novel approach to various trisubstituted oxazoles (28 examples, up to 88% yield) has been developed via 9H-thioxanthen-9-one (TX) mediated oxidative annulation of N-acetyl enamide under visible light irradiation in the presence of BF3 ⋅ Et2O (2.0 equiv) and 40 mol% of PhNO2. This metal-free procedure features high atom and step economy, green and mild conditions and broad substrate scope.

KW - Enamides

KW - Hydrogen atom Transfer

KW - Oxazoles

KW - Oxidative annulation

KW - Photocatalysis

UR - https://www.scopus.com/pages/publications/85146941113

U2 - 10.1002/ajoc.202300019

DO - 10.1002/ajoc.202300019

M3 - 文章

AN - SCOPUS:85146941113

SN - 2193-5807

VL - 12

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 5

M1 - e202300019

ER -

Visible-Light Induced Oxidative Annulation of Enamides to 2,4,5-Trisubstituted Oxazole Skeletons

Abstract

Keywords

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