Copper-Catalyzed Decarboxylative Atom Transfer Radical Addition of Iododifluoroacetate to Alkynyl Carboxylic Acids

被引：70

作者：

Li, Gang ^{[1
]}

Cao, Yi-Xuan ^{[1
]}

Luo, Chen-Guang ^{[1
]}

Su, Yi-Ming ^{[1
]}

Li, Yan ^{[1
]}

Lan, Quan ^{[1
]}

Wang, Xi-Sheng ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet & Self Assembly Chem Organ Funct, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

基金：

美国国家科学基金会;

关键词：

H-PHOSPHINE OXIDES; MEDIATED TRIFLUOROMETHYLATION; COUPLING REACTION; TERMINAL ALKYNES; FACILE SYNTHESIS; EFFICIENT; ALKENES; FLUORINE; DIFLUOROMETHYLATION; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.6b02216

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of copper-catalyzed decarboxylative atom transfer radical addition of alkynyl carboxylic acids has been developed with a readily available fluoroalkyl halide. This novel protocol has demonstrated a unique difunctionalization of nonterminal alkynes with a broad substrate scope and excellent functional-group tolerance. Mechanistic investigations revealed that the catalytic cycle was initiated by the attack of a difluoroalkyl radical to an in situ generated alkynylcopper species.

引用

页码：4806 / 4809

页数：4

共 50 条

[21] Light-Mediated Dual Phosphine-/Copper-Catalyzed Atom Transfer Radical Addition Reaction
Fedorov, Oleg V.
Scherbinina, Sofya I.
Levin, Vitalij V.
Dilman, Alexander D.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17) : 11068 - 11079
[22] Copper-Catalyzed Cascade Radical Addition Cyclization Halogen Atom Transfer between Alkynes and Unsaturated α-Halogenocarbonyls
Gao, Yuzhen
Zhang, Pengbo
Ji, Zhe
Tang, Guo
Zhao, Yufen
ACS CATALYSIS, 2017, 7 (01): : 186 - 190
[23] Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids
Wu, Ge
Zhou, Xueying
Wang, Caihong
CHINESE CHEMICAL LETTERS, 2022, 33 (10) : 4531 - 4535
[24] Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids
Feng, Chao
Loh, Teck-Peng
CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4779 - 4781
[25] Copper-Catalyzed Radical Addition of Alkynols to Synthesize Difluoroheterocyclic Compounds
Ke, Fumei
Yu, Changjiang
Li, Xin
Sheng, Heyun
Song, Qiuling
ORGANIC LETTERS, 2023, 25 (15) : 2733 - 2738
[26] Copper-Catalyzed Bis- or Trifunctionalization of Alkynyl Carboxylic Acids: An Efficient Route to Bis- and Tris-selenide Alkenes
Chen, Jing
Su, Shi-Xia
Hu, Da-Chao
Cui, Fei-Hu
Xu, Yan-Li
Chen, Yan-Yan
Ma, Xian-Li
Pan, Ying-Ming
Liang, Ying
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (05) : 892 - 896
[27] Synthesis of Diarylalkynes by Iron/Copper Co-Catalyzed Decarboxylative sp-sp2 Coupling of Alkynyl Carboxylic Acids and Aryl Halides
Li, Tingyi
Qu, Xiaoming
Zhu, Yan
Sun, Peng
Yang, Hailong
Shan, Yuqin
Zhang, Hongxin
Liu, Defu
Zhang, Xiang
Mao, Jincheng
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) : 2731 - 2738
[28] Copper-catalyzed selective difunctionalization of N-heteroarenes through a halogen atom transfer radical process
Fang, Hui-Lin
Sun, Qiu
Ye, Rong
Sun, Jing
Han, Ying
Yan, Chao-Guo
NEW JOURNAL OF CHEMISTRY, 2019, 43 (35) : 13832 - 13836
[29] Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids
Priebbenow, Daniel L.
Becker, Peter
Bolm, Carsten
ORGANIC LETTERS, 2013, 15 (24) : 6155 - 6157
[30] Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling
Gao, Bao
Xie, Yinjun
Shen, Zhiqiang
Yang, Lei
Huang, Hanmin
ORGANIC LETTERS, 2015, 17 (20) : 4968 - 4971

← 1 2 3 4 5 →