Nickel-Catalyzed Decarboxylative Difluoroalkylation of ,-Unsaturated Carboxylic Acids

被引：134

作者：

Li, Gang ^{[1
]}

Wang, Tao ^{[1
]}

Fei, Fan ^{[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：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 10期

基金：

美国国家科学基金会;

关键词：

fluoroalkylation; nickel; olefins; radicals; synthetic methods; COPPER-MEDIATED TRIFLUOROMETHYLATION; CROSS-COUPLING REACTIONS; ARYL BORONIC ACIDS; FACILE ACCESS; ARYLBORONIC ACIDS; ALKYL FLUORIDES; FLUOROALKYLATION; DIFLUOROMETHYLATION; ALKENES; FLUORINATION;

D O I：

10.1002/anie.201511321

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of nickel-catalyzed decarboxylative fluoroalkylation of ,-unsaturated carboxylic acids has been developed with commonly available fluoroalkyl halides. This novel transformation has demonstrated broad substrate scope, excellent functional-group tolerance, mild reaction conditions, and excellent stereoselectivity. Mechanistic investigations indicate that a fluoroalkyl radical is involved in the catalytic cycle.

引用

页码：3491 / 3495

页数：5

共 50 条

[41] Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides
Chen, Hui
Sun, Shuhao
Liao, Xuebin
ORGANIC LETTERS, 2019, 21 (10) : 3625 - 3630
[42] Novel System for Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids with Diacetoxyiodobenzene
Fursule, Ravindra Abhykumar
Patil, Pravin Onkar
Shewale, Bharti Devaji
Kosalge, Satish Bhaskar
Deshmukh, Prashant Krishnarao
Patil, Dilip Ashok
CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (11) : 1243 - 1245
[43] Nickel-catalyzed decarboxylative arylation of azoles with perfluoro- and nitrobenzoates
Crawford, Jennifer M.
Shelton, Kyle E.
Reeves, Emily K.
Sadarananda, Bryce K.
Kalyani, Dipannita
Organic Chemistry Frontiers, 2015, 2 (06): : 726 - 729
[44] Nickel-catalyzed Decarbonylative and Decarboxylative Cycloaddition of Isatoic Anhydrides with Alkynes
Nakai, Kenichiro
Kurahashi, Takuya
Matsubara, Seijiro
CHEMISTRY LETTERS, 2013, 42 (10) : 1238 - 1240
[45] Decarboxylative bromination of α,β-unsaturated carboxylic acids via an anodic oxidation
Bi, Mei-Xiang
Qian, Peng
Wang, Yu-Kang
Zha, Zheng-Gen
Wang, Zhi-Yong
CHINESE CHEMICAL LETTERS, 2017, 28 (06) : 1159 - 1162
[46] Decarboxylative bromination of α,β-unsaturated carboxylic acids via an anodic oxidation
Mei-Xiang Bi
Peng Qian
Yu-Kang Wang
Zheng-Gen Zha
Zhi-Yong Wang
ChineseChemicalLetters, 2017, 28 (06) : 1159 - 1162
[47] Nickel-catalyzed Decarboxylative Polymerization of 6-Alkynylisatoic Anhydride
Nakai, Kenichiro
Shiba, Takahiro
Yoshino, Yasufumi
Kurahashi, Talcuya
Matsubara, Seijiro
CHEMISTRY LETTERS, 2011, 40 (11) : 1240 - 1241
[48] Cu(II)-Mediated Decarboxylative Trifluoromethylthiolation of α,β-Unsaturated Carboxylic Acids
Cheng, Zhi-Fei
Tao, Ting-Ting
Feng, Yi-Si
Tang, Wei-Ke
Xu, Jun
Dai, Jian-Jun
Xu, Hua-Jian
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01): : 499 - 504
[49] Stereoretentive Decarboxylative Amidation of α,β-Unsaturated Carboxylic Acids to Access Enamides
Kweon, Jeonguk
Lee, Minjeong
Kim, Dongwook
Chang, Sukbok
ORGANIC LETTERS, 2024,
[50] Photoinduced Decarboxylative Difluoroalkylation and Perfluoroalkylation of α-Fluoroacrylic Acids
Lu, Xiao-Yu
Huang, Rui
Wang, Zi-Zhen
Zhang, Xiang
Jiang, Fan
Yang, Gui-Xian
Shui, Fu-Yi
Su, Meng-Xue
Sun, Yan-Xi
Sun, Hai-Lun
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09): : 6494 - 6505

← 1 2 3 4 5 →