Difluorocarbene enabled ester insertion/1,4-acyl rearrangement of 2-acetoxylpyridines: Modular access to gem-difluoromethylenated 2-pyridones

被引：5

作者：

Li, Shi-Wei ^{[1
]}

Wang, Gang ^{[1
]}

Ye, Zhi-Shi ^{[1
]}

机构：

[1] Dalian Univ Technol, Zhang Dayu Sch Chem, 2 Linggong Rd, Dalian 116024, Peoples R China

来源：

TETRAHEDRON LETTERS | 2023年 / 119卷

基金：

中国国家自然科学基金;

关键词：

Difluorocarbene; Rearrangement; 2-Pyridones; TRIMETHYLSILYL FLUOROSULFONYLDIFLUOROACETATE TFDA; FLUORINE; REAGENT; PHARMACEUTICALS; CYCLOPROPANES; ALKYLATION; ALDEHYDES; TMSCF2BR; TRENDS; ETHERS;

D O I：

10.1016/j.tetlet.2023.154413

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and simple protocol for the construction of gem-difluoromethylenated 2-pyridones via diflu-orocarbene enabled ester insertion/acyl rearrangement of 2-acetoxylpyridines and (bromodifluo-romethyl)trimethylsilane has been documented. The reactions feature transition-metal free, mild reaction conditions and excellent functional group compatibility. The late-stage modification of bioactive molecules, scaled-up reaction, and synthetic transformations demonstrated the practicability of this protocol.(c) 2023 Elsevier Ltd. All rights reserved.

引用

页数：6

共 3 条

[1] Access to N-Substituted 2-Pyridones by Catalytic Intermolecular Dearomatization and 1,4-Acyl Transfer
Xu, Guangyang
Chen, Ping
Liu, Pei
Tang, Shengbiao
Zhang, Xinhao
Sun, Jiangtao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 1980 - 1984
[2] Rhodium-Catalyzed Dearomative 1,4-Acyl Rearrangement of 2-Oxypyridines with Hydrazones: Access to N-Substituted 2-Pyridones
Ni, Yifeng
Sun, Jiangtao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (27)
[3] Rhodium-Catalyzed N-Arylation of 2-Pyridones Enabled by 1,6-Acyl Migratory Rearrangement of 2-Oxypyridines
Su, Jiahui
Yan, Zichun
Sun, Jiangtao
ORGANIC LETTERS, 2023, 25 (11) : 1974 - 1977

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