Thioesters synthesis: recent adventures in the esterification of thiols

被引:126
作者
Kazemi, Mosstafa [1 ]
Shiri, Lotfi [1 ]
机构
[1] Ilam Univ, Fac Basic Sci, Dept Chem, Ilam, Iran
关键词
thioester; organosulfur compounds; esterification; acylation; thiol; pharmaceutical; synthesis; SOLVENT-FREE CONDITIONS; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; IONIC LIQUIDS; CATALYZED ACYLATION; ROOM-TEMPERATURE; CARBOXYLIC-ACIDS; HETEROGENEOUS CATALYST; GRIGNARD-REAGENTS; CONVENIENT METHOD;
D O I
10.1080/17415993.2015.1075023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thioesters are important class of organosulfur compounds that play a fundamental role in the construction of pharmaceutical, biological, industrial and natural products. In this respect, thioesters synthesis is one of the most important tasks in organosulfur chemistry. The esterification of thiols is the best and most common strategy for the synthesis of thioesters. During the last decade (from 2005 to 2015), the application of a diverse range of reagents as activating or promoter agents for the acylation of thiols in order to synthesize thioesters have been investigated by various research teams. In this review, we have summarized and studied recently reported synthetic protocols in the arena of acylation of thiols. [GRAPHICS] .
引用
收藏
页码:613 / 623
页数:11
相关论文
共 67 条
[1]   o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Venturello, Paolo .
SYNTHESIS-STUTTGART, 2008, 22 (22) :3625-3632
[2]   A HIGHLY EFFICIENT SYNTHETIC ROUTE TO KETONES THROUGH SEQUENTIAL COUPLING REACTIONS OF GRIGNARD-REAGENTS WITH S-PHENYL CARBONOCHLORIDOTHIOATE IN THE PRESENCE OF NICKEL OR IRON CATALYSTS [J].
CARDELLICCHIO, C ;
VIANDANESE, V ;
MARCHESE, G ;
RONZINI, L .
TETRAHEDRON LETTERS, 1985, 26 (30) :3595-3598
[3]   Highly Efficient Catalyst Derived From Ni-Fe-Hydrotalcite for Solvent-Free O- or S-Acetylation of Alcohols, Phenols and Thiols at Room Temperature [J].
Choudhary, Vasant R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES INDIA SECTION A-PHYSICAL SCIENCES, 2013, 83 (01) :15-19
[4]   EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].
COREY, EJ ;
NICOLAOU, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616
[5]  
Crux C., 1994, TETRAHEDRON, V50, P10321, DOI DOI 10.1016/S0040-4020(01)81764-6
[6]   A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite® [J].
Dan, Weixing ;
Deng, Hongjuan ;
Chen, Jiuxi ;
Liu, Miaochang ;
Ding, Jinchang ;
Wu, Huayue .
TETRAHEDRON, 2010, 66 (37) :7384-7388
[7]   Silver Triflate Catalyzed Acetylation of Alcohols, Thiols, Phenols, and Amines [J].
Das, Rima ;
Chakraborty, Debashis .
SYNTHESIS-STUTTGART, 2011, (10) :1621-1625
[8]   Reaction of acyl chlorides with organometallic reagents: A banquet table of metals for ketone synthesis [J].
Dieter, RK .
TETRAHEDRON, 1999, 55 (14) :4177-4236
[9]   Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa(thia)zoles [J].
Duarte, Anai ;
Cunico, Wilson ;
Pereira, Claudio M. P. ;
Flores, Alex F. C. ;
Freitag, Rogerio A. ;
Siqueira, Geonir M. .
ULTRASONICS SONOCHEMISTRY, 2010, 17 (02) :281-283
[10]   AN EFFICIENT SYNTHESIS OF THIOESTERS VIA TFA-CATALYZED REACTION OF CARBOXYLIC ACID AND THIOLS: REMARKABLY FACILE C-S BOND FORMATION [J].
El-Azab, Adel S. ;
Abdel-Aziz, Alaa A. -M. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (09) :1046-1055