Lamar Angus A, Liebeskind Lanny S
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, OK 74104, USA.
Sanford S. Atwood Chemistry Center, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA.
Tetrahedron Lett. 2015 Oct 28;56(44):6034-6037. doi: 10.1016/j.tetlet.2015.09.050. Epub 2015 Sep 21.
The first organo-catalyzed silylthioesterification of a carboxylic acid and a commercially available mercaptoorganosilane results in the in situ production of an -silylthionoester. Subsequent amine addition forms amides in an operationally simple one-pot procedure without removal of water. The scope and efficiency of these reactions with respect to the catalyst, carboxylic acid, amine, [Si─S] moiety, and solvent are investigated. A number of functionalities are tolerated in the two-step amidation including alkene, alkyne, alkyl and aryl halides, benzylic ethers, and heterocycles with free coordinating sites.
羧酸与市售巯基有机硅的首次有机催化甲硅烷基硫酯化反应原位生成了甲硅烷基硫代酸酯。随后加入胺,在无需除水的情况下,通过操作简单的一锅法形成酰胺。研究了这些反应在催化剂、羧酸、胺、[Si─S]部分和溶剂方面的范围和效率。两步酰胺化反应中可以耐受多种官能团,包括烯烃、炔烃、烷基和芳基卤化物、苄基醚以及具有自由配位位点的杂环。