Recent advances in the chemistry of organic thiocyanates

被引:306
作者
Castanheiro, Thomas [1 ]
Suffert, Jean [1 ]
Donnard, Morgan [1 ]
Gulea, Mihaela [1 ]
机构
[1] Univ Strasbourg, Fac Pharm, CNRS, Lab Innovat Therapeut UMR 7200, 74 Route Rhin, F-67401 Illkirch Graffenstaden, France
关键词
MICROWAVE-ASSISTED SYNTHESIS; ONE-POT SYNTHESIS; TRIFLUOROMETHYL SULFIDES; SUBSTITUTION-REACTIONS; POTASSIUM THIOCYANATE; ALLYLIC THIOCYANATES; ARYL THIOCYANATES; EFFICIENT; THIOETHERS; ALKYNES;
D O I
10.1039/c5cs00532a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Organic thiocyanates are important synthetic intermediates to access valuable sulfur-containing compounds. In this review the different methods for their preparation and their synthetic applications will be presented. The literature of the last 15 years will be covered, highlighting selected recent advances in the chemistry of this class of compounds. We hope to offer chemists the tools to have a good grasp of this singular functionality and open the door to further progress in this chemistry.
引用
收藏
页码:494 / 505
页数:12
相关论文
共 51 条
[1]   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
[2]   Catalytic thiocyanation of aryldiazonium salts in the presence of copper salts [J].
Beletskaya, Irina P. ;
Sigeev, Alexander S. ;
Peregudov, Alexander S. ;
Petrovskii, Pavel V. .
MENDELEEV COMMUNICATIONS, 2006, 16 (05) :250-251
[3]   Simple and quick preparation of α-thiocyanate ketones in hydroalcoholic media. Access to 5-aryl-2-imino-1,3-oxathiolanes [J].
Bisogno, Fabricio R. ;
Cuetos, Anibal ;
Lavandera, Ivan ;
Gotor, Vicente .
GREEN CHEMISTRY, 2009, 11 (04) :452-454
[4]   Peptide/Protein Stapling and Unstapling: Introduction of s-Tetrazine, Photochemical Release, and Regeneration of the Peptide/Protein [J].
Brown, Stephen P. ;
Smith, Amos B., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (12) :4034-4037
[5]   Practical Access to Aromatic Thiocyanates by CuCN-Mediated Direct Aerobic Oxidative Cyanation of Thiophenols and Diaryl Disulfides [J].
Castanheiro, Thomas ;
Gulea, Mihaela ;
Donnard, Morgan ;
Suffert, Jean .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (35) :7814-7817
[6]   An intramolecular [2+3] cycloaddition route to fused 5-heterosubstituted tetrazoles [J].
Demko, ZP ;
Sharpless, KB .
ORGANIC LETTERS, 2001, 3 (25) :4091-4094
[7]   Preparation of 5-substituted 1H-tetrazoles from nitriles in water [J].
Demko, ZP ;
Sharpless, KB .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7945-7950
[8]   The chemistry of thiocyanic esters [J].
Erian, AW ;
Sherif, SM .
TETRAHEDRON, 1999, 55 (26) :7957-8024
[9]   A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles [J].
Fan, Weigang ;
Yang, Qi ;
Xu, Fengshan ;
Li, Pixu .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) :10588-10592
[10]   Facile ring-expansion substitution reactions of 1,3-dithiolanes and 1,3-dithianes initiated by electrophilic reagents to produce monohalo-, -cyano-, -azido- and -thiocyanato-1,4-dithiins and-1,4-dithiepins [J].
Firouzabadi, H ;
Iranpoor, N ;
Garzan, A ;
Shaterian, HR ;
Ebrahimzadeh, F .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (02) :416-428