Synthesis of Monofluoromethylthioesters from Aldehydes

被引：30

作者：

Guo, Shi-Huan ^{[1
]}

Wang, Meng-Yue ^{[1
]}

Pan, Gao-Fei ^{[1
]}

Zhu, Xue-Qing ^{[1
]}

Gao, Ya-Ru ^{[1
]}

Wang, Yong-Qiang ^{[1
]}

机构：

[1] Northwest Univ, Dept Chem & Mat Sci, Minist Educ, Key Lab Synthet & Nat Funct Mol Chem, Xian 710069, Shaanxi, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Aldehydes; Fluorides; Radical reactions; Synthetic methods; Monofluoromethylthioesters; ALPHA; BETA-UNSATURATED ACYL RADICALS; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; DIELECTRIC-PROPERTIES; CATALYZED SYNTHESIS; BORONIC ACIDS; FLUORINE; ARYL; DIFLUOROMETHYLTHIOLATION; DECOMPOSITION; CYCLIZATION;

D O I：

10.1002/adsc.201800136

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A direct and efficient approach to the synthesis of monofluoromethylthioesters from aldehydes has been developed. The synthetic method features mild reaction conditions, good tolerance of functional groups, a broad substrate scope, and especially no metal involved in the reaction. The approach has the potential to be an important tool for the late-stage functionalization of advanced synthetic intermediates, and may find many applications in medicinal chemistry.

引用

页码：1861 / 1869

页数：9

共 68 条

[1] Photochemically induced radical alkenylation of C(sp3)-H bonds [J].

Amaoka, Yuuki ;

Nagatomo, Masanori ;

Watanabe, Mizuki ;

Tao, Keisuke ;

Kamijo, Shin ;

Inoue, Masayuki .

CHEMICAL SCIENCE, 2014, 5 (11) :4339-4345

[2]

[Anonymous], 2013, Angew. Chem, DOI [10.1002/ange.201209817, DOI 10.1002/ANGE.201209817]

[3]

[Anonymous], 2011, Angew. Chem., DOI [10.1002/ange.201102543, DOI 10.1002/ANGE.201102543]

[4]

[Anonymous], 2013, Angew. Chem., DOI DOI 10.1002/ANGE.201301634

[5]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201205156

[6]

[Anonymous], 2013, ANGEW CHEM, DOI [DOI 10.1002/ANGE.201206566, 10.1002/ange.201206566]

[7] Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides [J].

Baert, Francois ;

Colomb, Julie ;

Billard, Thierry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10382-10385

[8]

Bayarmagnai B., 2015, ANGEW CHEM, V127, P5845, DOI 10.1002/ange.201500899

[9] Synthesis of Difluoromethyl Thioethers from Difluoromethyl Trimethylsilane and Organothiocyanates Generated In Situ [J].

Bayarmagnai, Bilguun ;

Matheis, Christian ;

Jouvin, Kevin ;

Goossen, Lukas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5753-5756

[10] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

← 1 2 3 4 5 6 7 →