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

[41] Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Sathyamoorthi, Shyam
Du Bois, J.
ORGANIC LETTERS, 2016, 18 (24) : 6308 - 6311
[42] Copper-catalyzed protodecarboxylation of aromatic carboxylic acids
Goossen, Lukas J.
Thiel, Werner R.
Rodriguez, Nuria
Linder, Christophe
Melzer, Bettina
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (14-15) : 2241 - 2246
[43] Copper-Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines
Choi, Jinseop
Lim, Jeongah
Irudayanathan, Francis Mariaraj
Kim, Han-Sung
Park, Jaerim
Yu, Su Been
Jang, Yuna
Raja, Gabriel Charles Edwin
Nam, Kye Chun
Kim, Jimin
Lee, Sunwoo
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (06) : 770 - 777
[44] Phosphane-Free Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Halides under Aerobic Conditions (September, pg 4751, 2011)
Pan, Delin
Zhang, Chun
Ding, Shengtao
Jiao, Ning
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (29) : 5919 - 5919
[45] Copper-Catalyzed Decarboxylative Difluoromethylation
Zeng, Xiaojun
Yan, Wenhao
Zacate, Samson B.
Chao, Tzu-Hsuan
Sun, Xiaodong
Cao, Zhi
Bradford, Kate G. E.
Paeth, Matthew
Tyndall, Sam B.
Yang, Kundi
Kuo, Tung-Chun
Cheng, Mu-Jeng
Liu, Wei
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) : 11398 - 11403
[46] Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids
Feng, Chao
Loh, Teck-Peng
CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4779 - 4781
[47] Photoinduced copper-catalyzed dual decarboxylative coupling of α,β-unsaturated carboxylic acids with redox-active esters
Lu, Xiao-Yu
Gao, Ang
Liu, Qi-Le
Xia, Ze-Jie
TETRAHEDRON, 2021, 92
[48] Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines
Pimpasri, Chaleena
Sumunnee, Ladawan
Yotphan, Sirilata
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (20) : 4320 - 4327
[49] Red-Light-Induced, Copper-Catalyzed Atom Transfer Radical Polymerization
Dadashi-Silab, Sajjad
Kim, Khidong
Lorandi, Francesca
Szczepaniak, Grzegorz
Kramer, Stephanie
Peteanu, Linda
Matyjaszewski, Krzysztof
ACS MACRO LETTERS, 2022, 11 (03) : 376 - 381
[50] Polychloroalkane initiators in copper-catalyzed atom transfer radical polymerization of (meth)acrylates
Destarac, M
Matyjaszewski, K
Boutevin, B
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2000, 201 (02) : 265 - 272

← 1 2 3 4 5 →