Synthesis of gem-Difluorinated 1,4-Dienes via Nickel-Catalyzed Three-Component Coupling of (Trifluoromethyl)alkenes, Alkynes, and Organoboronic Acids

被引：6

作者：

Zhang, Xu ^{[1
,2
]}

Huang, Xinmiao ^{[1
,2
]}

Chen, Yingzhuang ^{[1
,2
]}

Chen, Bo ^{[1
,2
]}

Ma, Yuanhong ^{[1
,2
]}

机构：

[1] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Key Lab Phytochemistry R&D Hunan Prov, Minist Educ, Changsha 410081, Peoples R China

[2] Hunan Normal Univ, Inst Interdisciplinary Studies, Coll Chem & Chem Engn, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 10期

基金：

中国国家自然科学基金;

关键词：

MARINE SPONGE;

D O I：

10.1021/acs.orglett.3c00444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a nickel-catalyzed defluorinative three -component coupling of trifluoromethyl alkenes, internal alkynes, and organoboronic acids is presented. The protocol provides a highly efficient and selective route for the synthesis of structurally diverse gem-difluorinated 1,4-dienes under mild conditions. Mechanistic studies suggest that C-F bond activation proceeds probably through the oxidative cyclization of trifluoromethyl alkenes with Ni(0) species, sequential addition to alkynes, and beta- fluorine elimination. + R2 = R3 + R4-B(OH)2 R1 CF3 O mild conditions O wide substrate scope R4 Nickel catalysis F / R3 R1 R2 O high chemo-, regio-and stereoselectivity

引用

页码：1748 / 1753

页数：6

共 50 条

[1] Nickel-catalyzed regio- and diastereoselective intermolecular three-component coupling of oxabicyclic alkenes with alkynes and organoboronic acids
Mannathan, Subramaniyan
Cheng, Chien-Hong
CHEMICAL COMMUNICATIONS, 2013, 49 (15) : 1557 - 1559
[2] Nickel-Catalyzed Multicomponent Coupling of Butadiene, Aldehydes, Alkynes and Schwartz Reagent to Form 1,4-Dienes
Li, Yu-Qing
Shi, Shi-Liang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (05) : 1939 - 1948
[3] Synthesis of gem-Difluorinated 1,3-Dienes via Synergistic Cu/Pd-Catalyzed Borodifluorovinylation of Alkynes
Xu, Wen-Yan
Li, Yu-Jie
Gong, Tian-Jun
Fu, Yao
ORGANIC LETTERS, 2022, 24 (32) : 5884 - 5889
[4] Three-component reaction of gem-difluorinated cyclopropanes with alkenes and B2pin2 for the synthesis of monofluoroalkenes
Suliman, Ayman M. Y.
Ahmed, Ebrahim-Alkhalil M. A.
Gong, Tian-Jun
Fu, Yao
CHEMICAL COMMUNICATIONS, 2021, 57 (52) : 6400 - 6403
[5] Highly Selective Nickel-Catalyzed Three-Component Coupling of Alkynes with Enones and Alkenyl Boronic Acids: A Novel Route to Substituted 1,3-Dienes
Yang, Chun-Ming
Jeganmohan, Masilamani
Parthasarathy, Kanniyappan
Cheng, Chien-Hong
ORGANIC LETTERS, 2010, 12 (16) : 3610 - 3613
[6] Nickel-Catalyzed Three-Component 1,2-Carboacylation of Alkenes
Jin, Shengzhou
Wang, Lanfen
Jia, Yinggang
Ma, Wenbo
Wang, Dingyi
MOLECULES, 2024, 29 (18):
[7] Synthesis of gem-Difluoroalkenes via Ni-Catalyzed Three-Component Defluorinative Reductive Cross-Coupling of Organohalides, Alkenes and Trifluoromethyl Alkenes
Ma, Teng
Li, Xiao
Ping, Yuanyuan
Kong, Wangqing
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (18) : 2212 - 2218
[8] Nickel-catalyzed three-component coupling reaction of terminal alkynes, dihalomethane and amines to propargylamines
Lanke, Satish R.
Bhanage, Bhalchandra M.
APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (12) : 729 - 733
[9] Synthesis of gem-difluoroalkenes via nickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides
Lu, Xiao-Yu
Jiang, Run-Chuang
Li, Jia-Mei
Liu, Chuang-Chuang
Wang, Qing-Qing
Zhou, Hai-Pin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (19) : 3674 - 3678
[10] Nickel-Catalyzed Three-Component [2+2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes
Qiu, Zaozao
Xie, Zuowei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5729 - 5732

← 1 2 3 4 5 →