Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

被引：19

作者：

Yan, Zhiyang ^{[1
]}

Sun, Bin ^{[1
]}

Huang, Panyi ^{[2
]}

Zhao, Haiyun ^{[1
]}

Ding, Hao ^{[2
]}

Su, Weike ^{[1
]}

Jin, Can ^{[1
,2
]}

机构：

[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Peoples R China

[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2022年 / 33卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Photocatalysis; Oxazolines; Allylic amide; N-Hydroxyphthalimide ester; Alkylation/cyclization; Decarboxylation; DECARBOXYLATIVE ALKYLATION; METAL-FREE; PHOTOREDOX; COMPLEXES; ACID; PHOTOCATALYST; CYCLIZATION; INHIBITORS; CATALYSIS;

D O I：

10.1016/j.cclet.2021.09.067

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

引用

页码：1997 / 2000

页数：4

共 49 条

[1] Visible-Light-Promoted Decarboxylative Alkylation/Cyclization of Vinylcycloalkanes
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[2] Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N -Hydroxyphthalimide Ester
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[3] Synthesis of Polycyclic Quinazolinones through C(sp3)-H Functionalization of Inert Alkanes or Visible-Light-Promoted Oxidation Decarboxylation of N-Hydroxyphthalimide Esters
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (35)
[4] Visible light-induced radical cascade reaction of acryloylbenzamides with N-hydroxyphthalimide esters
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TETRAHEDRON LETTERS, 2022, 95
[5] Visible-Light-Promoted Atom Transfer Radical Cyclization of Unactivated Alkyl Iodides
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[6] 9,10-Phenanthrenedione-Catalyzed, Visible-Light-Promoted Radical Intramolecular Cyclization of N-Biarylglycine Esters: One-Pot synthesis of Phenanthridine-6-Carboxylates
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[8] Visible-Light-Promoted Fe(III)-Catalyzed N-H Alkylation of Amides and N-Heterocycles
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[9] Visible light photoredox catalysis with N-hydroxyphthalimide for [4+2] cyclization between N-methylanilines and maleimides
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[10] Visible-Light-Induced C2 Alkylation of Heterocyclic N-Oxides with N-Hydroxyphthalimide Esters under Metal-Free Conditions
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