α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

被引：29

作者：

Wang, Xu ^{[1
]}

Wu, Zijun ^{[1
]}

Wang, Jian ^{[1
]}

机构：

[1] Tsinghua Univ, Sch Med, Dept Pharmacol & Pharmaceut Sci, Beijing 117543, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 03期

关键词：

ENANTIOSELECTIVE FLUORINATION; ASYMMETRIC FLUORINATION; EFFICIENT SYNTHESIS; BETA-KETOESTERS; UMPOLUNG; ALLENES; TRIFLUOROMETHYLATION; ORGANOCATALYSIS; GENERATION; ALDEHYDES;

D O I：

10.1021/acs.orglett.5b03615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

引用

页码：576 / 579

页数：4

共 50 条

[41] N-heterocyclic carbene-catalyzed arene formation reactions
Tingting Li
Zhichao Jin
Yonggui Robin Chi
Science China Chemistry, 2022, 65 : 210 - 223
[42] N-Heterocyclic Carbene-Catalyzed Enantioselective Synthesis of Spiro-glutarimides via α,β-Unsaturated Acylazoliums
Mondal, Santigopal
Ghosh, Arghya
Mukherjee, Subrata
Biju, Akkattu T.
ORGANIC LETTERS, 2018, 20 (15) : 4499 - 4503
[43] N-Heterocyclic carbene-catalyzed dehydration of α,ω-disilanol oligomers
Marrot, Sebastien
Bonnette, Fabien
Kato, Tsuyoshi
Saint-Jalmes, Laurent
Fleury, Etienne
Baceiredo, Antoine
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (10) : 1729 - 1732
[44] N-Heterocyclic Carbene-Catalyzed Convenient Benzonitrile Assembly
Jia, Qianfa
Wang, Jian
ORGANIC LETTERS, 2016, 18 (09) : 2212 - 2215
[45] N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions
Song, Jinhua J.
Tan, Zhulin
Reeves, Jonathan T.
Yee, Nathan K.
Senanayake, Chris H.
ORGANIC LETTERS, 2007, 9 (06) : 1013 - 1016
[46] N-Heterocyclic Carbene-Catalyzed Generation of α,β-Unsaturated Acyl Imidazoliums: Synthesis of Dihydropyranones by their Reaction with Enolates
Ryan, Sarah J.
Candish, Lisa
Lupton, David W.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) : 14176 - +
[47] N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Ishii, Takuya
Kakeno, Yuki
Nagao, Kazunori
Ohmiya, Hirohisa
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (09) : 3854 - 3858
[48] N-heterocyclic carbene-catalyzed nucleophilic aroylation of fluorobenzenes
Suzuki, Yumiko
Ota, Shinya
Fukuta, Yoshinori
Ueda, Yuki
Sato, Masayuki
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06): : 2420 - 2423
[49] N-heterocyclic carbene-catalyzed arene formation reactions
Li, Tingting
Jin, Zhichao
Chi, Yonggui Robin
SCIENCE CHINA-CHEMISTRY, 2022, 65 (02) : 210 - 223
[50] N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones
Atienza, Roxanne L.
Roth, Howard S.
Scheidt, Karl A.
CHEMICAL SCIENCE, 2011, 2 (09) : 1772 - 1776

← 1 2 3 4 5 →