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

[21] Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes
Raja, Gabriel Charles Edwin
Irudayanathan, Francis Mariaraj
Kim, Han-Sung
Kim, Jimin
Lee, Sunwoo
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12): : 5244 - 5249
[22] Selective Nickel- and Manganese-Catalyzed Decarboxylative Cross Coupling of Some α,β-Unsaturated Carboxylic Acids with Cyclic Ethers
Zhang, Jia-Xiang
Wang, Yan-Jing
Zhang, Wei
Wang, Nai-Xing
Bai, Cui-Bing
Xing, Ya-Lan
Li, Yi-He
Wen, Jia-Long
SCIENTIFIC REPORTS, 2014, 4
[23] Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes
Ai, Zhenkang
Chen, Hui
Liao, Xuebin
CHINESE CHEMICAL LETTERS, 2025, 36 (03)
[24] Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes
Zhenkang Ai
Hui Chen
Xuebin Liao
Chinese Chemical Letters, 2025, 36 (03) : 281 - 286
[25] Selective Nickel- and Manganese-Catalyzed Decarboxylative Cross Coupling of Some α,β-Unsaturated Carboxylic Acids with Cyclic Ethers
Jia-Xiang Zhang
Yan-Jing Wang
Wei Zhang
Nai-Xing Wang
Cui-Bing Bai
Ya-Lan Xing
Yi-He Li
Jia-Long Wen
Scientific Reports, 4
[26] Nickel-Catalyzed Carboxylation of Conjugated Dienes with Carbon Dioxide and DIBAL-H for the Synthesis of β,γ-Unsaturated Carboxylic Acids
Luo, Ying
Chan, Bun
Fukuda, Tsutomu
Onodera, Gen
Kimura, Masanari
SYNLETT, 2021, 32 (15) : 1551 - 1554
[27] Nickel-Catalyzed Reductive Coupling of Carboxylic Acids with Disulfides to Access Thioesters
Wu, Kang
Wang, Tian-Zhang
Liang, Yu-Feng
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4233 - 4240
[28] Nickel-Catalyzed ortho-Acyloxylation of Benzamides and Acrylamides with Carboxylic Acids
Lin, Jingyi
Guo, Zhao
Lin, Cong
Gao, Fei
Shen, Liang
CHEMISTRYSELECT, 2020, 5 (06): : 1925 - 1928
[29] Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids
Chen, Qiang
Fan, Xin-Heng
Zhang, Li-Peng
Yang, Lian-Ming
RSC ADVANCES, 2014, 4 (96) : 53885 - 53890
[30] Nickel-Catalyzed Reductive Decarboxylative/Deaminative Glycosylation of Activated Aliphatic Acids and Primary Amines
Liu, Xu-Ge
Yang, Qian
Liu, Deng-Yin
Liu, Jing
Tan, Dong-Hang
Ruan, Yu-Jun
Wang, Peng-Fei
Wang, Xiao-Li
Wang, Honggen
ORGANIC LETTERS, 2023, 25 (27) : 5022 - 5026

← 1 2 3 4 5 →