Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles

被引：18

作者：

Ding, Tianqi ^{[1
]}

Jiang, Lvqi ^{[1
]}

Yi, Wenbin ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 28期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

ONE-POT THIOETHERIFICATION; ALPHA-FLUORINATED ETHERS; ARYL HALIDES; AMINES; THIOUREA; SULFUR; DIFLUOROCARBENE; DEUTERATION; GENERATION; CHEMISTRY;

D O I：

10.1039/c9cc09709k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the "H" source to the most commonly used "D" sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.

引用

页码：3995 / 3998

页数：4

共 71 条

[1] [Anonymous], 1982, Biomedical Aspects of Fluorine Chemistry
[2] Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences
Atzrodt, Jens
Derdau, Volker
Kerr, William J.
Reid, Marc
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) : 1758 - 1784
[3] Synthesis of Difluoromethyl Thioethers from Difluoromethyl Trimethylsilane and Organothiocyanates Generated In Situ
Bayarmagnai, Bilguun
Matheis, Christian
Jouvin, Kevin
Goossen, Lukas J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) : 5753 - 5756
[4] EFFECT OF DEUTERIUM SUBSTITUTION IN SYMPATHOMIMETIC AMINES ON ADRENERGIC RESPONSES
BELLEAU, B
BURBA, J
[J]. SCIENCE, 1961, 133 (344) : 102 - &
[5] Difluoromethylation and gem-difluorocyclopropenation with difluorocarbene generated by decarboxylation
Deng, Xiao-Yun
Lin, Jin-Hong
Zheng, Jian
Xiao, Ji-Chang
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (42) : 8805 - 8808
[6] One-Pot Synthesis of Difluoromethyl Thioethers from Thiourea and Diethyl Bromodifluoromethylphosphonate
Ding, Tianqi
Jiang, Lvqi
Yi, Wenbin
[J]. ORGANIC LETTERS, 2018, 20 (01) : 170 - 173
[7] Isotope chemistry; a useful tool in the drug discovery arsenal
Elmore, Charles S.
Bragg, Ryan A.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (02) : 167 - 171
[8] Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry
Feng, Minghao
Tang, Bingqing
Liang, Steven H.
Jiang, Xuefeng
[J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) : 1200 - 1216
[9] Synthesis of Difluoromethyl Ethers with Difluoromethyltriflate
Fier, Patrick S.
Hartwig, John F.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) : 2092 - 2095
[10] One-Pot Thioetherification of Aryl Halides Using Thiourea and Alkyl Bromides Catalyzed by Copper(I) Iodide Free from Foul-Smelling Thiols in Wet Polyethylene Glycol (PEG 200)
Firouzabadi, Habib
Iranpoor, Nasser
Gholinejad, Mohammad
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (01) : 119 - 124

← 1 2 3 4 5 6 7 8 →