54829-38-8Relevant academic research and scientific papers
Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
, p. 8225 - 8228 (2019/07/16)
A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.
Microwave-assisted direct thioesterification of carboxylic acids
Chou, Yen-Lin,Jhong, Yi,Swain, Sharada Prasanna,Hou, Duen-Ren
, p. 10201 - 10208 (2018/05/31)
A one-pot synthesis of thioesters directly from carboxylic acids, N,N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4- (dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the quaternary ammonium salts, derived from alkyl halides and tertiary amines, were the intermediates to yield thioesters. A new reaction mechanism for this thioesterification is proposed.
A novel approach for the direct conversion of alkylsulfonyl derivatives into alkylcarbonyl derivatives via tin-free radical carbonylation
Kim, Sangmo,Lim, Kyoung-Chan,Kim, Sunggak
, p. 4507 - 4509 (2008/04/01)
A novel radical approach for the direct conversion of RSO2X into RCOX in a single step is devised; the present approach is very simple, highly efficient, and minimizes formation of by-product. The Royal Society of Chemistry.
A convenient method for the synthesis of carboxamides and thioesters by using tetrakis(2-methylimidazol-1-yl)silane
Tozawa, Takashi,Yamane, Yoshinobu,Mukaiyama, Teruaki
, p. 629 - 641 (2007/10/03)
Tetrakis(2-methylimidazol-1-yl)silane [Si(2-Me-Im)4], a new dehydrating reagent having silicon-imidazole linkage, reacted readily with carboxylic acids at room temperature to form the corresponding 1-acyl-2-methylimidazole intermediates, which smoothly underwent subsequent condensation with nucleophiles such as amines or thiols to afford the corresponding carboxamides or thioesters in good to excellent yields, respectively.
Direct transformation of carboxyclic acids to thiol esters induced by phenyl dichlorophosphate
Liu, Hsing-Jang,Sabesan, Subramaniam Iyer
, p. 2645 - 2648 (2007/10/02)
The condensation of carboxylic acids and thiols is greatly facilitated by the use of phenyl dichlorophosphate as an activating agent giving thiol esters in good yields.
