Oxidative Trifluoromethylthiolation of Terminal Alkynes with AgSCF3: A Convenient Approach to Alkynyl Trifluoromethyl Sulfides

被引：55

作者：

Zhu, Sheng-Qing ^{[1
]}

Xu, Xiu-Hua ^{[1
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 21期

基金：

中国国家自然科学基金;

关键词：

Synthetic methods; Alkynes; Sulfur; Silver; Oxidation; ARYL BORONIC ACIDS; COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION; HYPERVALENT IODINE REAGENT; ALPHA-FLUORINATED ETHERS; NUCLEOPHILIC TRIFLUOROMETHYLTHIOLATION; ELECTROPHILIC TRIFLUOROMETHANESULFANYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLTHIOLATION; SUBSTITUENT CONSTANTS; DERIVATIVES; GENERATION;

D O I：

10.1002/ejoc.201402533

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the efficient synthesis of alkynyl trifluoromethyl sulfides was developed. By combining AgSCF3 and NCS in N,N-dimethylacetamide, an electrophilic active intermediate was produced, which was then treated with a variety of terminal alkynes to afford the corresponding trifluoromethanesulfenylated products in moderate to excellent yields.

引用

页码：4453 / 4456

页数：4

共 50 条

[41] A convenient synthesis of CF3-containing alkynyl imines by a copper-free Sonogashira coupling of imidoyl chlorides with terminal alkynes
Chen, Muwang
Zhang, Qiaochu
Zhang, Xingguo
Zhong, Ping
Hu, Maolin
JOURNAL OF CHEMICAL RESEARCH, 2008, (11) : 637 - 639
[42] A convenient approach to 3-trifluoromethyl-6-azaindoles
Ivonin, Sergey P.
Yurchenko, Aleksandr A.
Voloshchuk, Volodymyr V.
Yurchenko, Sergey A.
Rusanov, Eduard B.
Pirozhenko, Vladimir V.
Volochnyuk, Dmitriy M.
Kostyuk, Aleksandr N.
JOURNAL OF FLUORINE CHEMISTRY, 2020, 233
[43] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source
Chu, Lingling
Qing, Feng-Ling
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) : 1513 - 1522
[44] Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles
Uppalabat, Thikhamporn
Hassa, Nattawoot
Sawektreeratana, Natthapat
Leowanawat, Pawaret
Janthakit, Pattarapapa
Nalaoh, Phattananawee
Promarak, Vinich
Soorukram, Darunee
Reutrakul, Vichai
Kuhakarn, Chutima
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 5403 - 5419
[45] Cu(I)-catalyzed coupling reactions of fluorinated imidoyl halides with terminal alkynes: Convenient synthesis of fluorinated alkynyl imines
Li, Shan
Zhu, Jiangtao
Xie, Haibo
Chen, Zixian
Wu, Yongming
JOURNAL OF FLUORINE CHEMISTRY, 2011, 132 (03) : 196 - 201
[46] Tandem trifluoromethylthiolation and cyclization of N-aryl-3-butenamides with AgSCF3: divergent access to CF3S-substituted 3,4-dihydroquinolin-2-ones and azaspiro[4,5]dienones
Wang, Liang
Xie, Lin
Fang, Zeguo
Zhang, Qian
Li, Dong
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (11): : 3061 - 3067
[47] Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkynes and Aryl Boronic Acids Using (Trifluoromethyl)trimethylsilane
Jiang, Xueliang
Chu, Lingling
Qing, Feng-Ling
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (03): : 1251 - 1257
[48] A photosensitized metal free approach to α-ketoamides: sequential oxidative amidationdiketonization of terminal alkynes
Manhas, Farah Manzer
Raheem, Shabnam
Kumar, Jaswant
Thakur, Pankaj
Rizvi, Masood Ahmad
CHEMISTRYSELECT, 2021, 6 (29): : 7499 - 7504
[49] AgSCF3-Mediated Oxidative Trifluoromethythiolation of Alkynes with Dearomatization to Synthesize SCF3-Substituted Spiro[4,5]trienones
Jin, Dong-Po
Gao, Pin
Chen, Dao-Qian
Chen, Si
Wang, Jia
Liu, Xue-Yuan
Liang, Yong-Min
ORGANIC LETTERS, 2016, 18 (14) : 3486 - 3489
[50] A heterogeneous copper(I)-catalyzed aerobic oxidative cross-dehydrogenative coupling of terminal allcynes with thiols leading to alkynyl sulfides
Fang, Zhiqiang
He, Wen
Cai, Mingzhong
Lin, Yang
Zhao, Hong
TETRAHEDRON LETTERS, 2015, 56 (46) : 6463 - 6467

← 1 2 3 4 5 →