Rapid and convenient thioester synthesis under phase-transfer catalysis conditions
C Simion, I Hashimoto, Y Mitoma…
Index: Simion, Cristian; Hashimoto, Iwao; Mitoma, Yoshiharu; Simion, Alina Marieta; Egashira, Naoyoshi Phosphorus, Sulfur and Silicon and the Related Elements, 2010 , vol. 185, # 12 p. 2480 - 2488
Full Text: HTML
Citation Number: 3
Abstract
Various thioesters were obtained through an efficient phase-transfer catalysis method, by treating several thiophenols with different acyl chlorides, in a biphasic system composed of 10% aqueous NaOH and dichloromethane in the presence of tetrabutylammonium chloride. The thiolation reaction was complete in only 5 minutes, at 0° C.
Related Articles:
[Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Letters, 1985 , vol. 26, # 30 p. 3595 - 3598]
[Miyashita, Mitsutomo; Shiina, Isamu; Miyoshi, So; Mukaiyama, Teruaki Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 5 p. 1516 - 1527]
A simple synthesis of thiol esters from copper-I-mercaptides and acyl chlorides
[Reissig, Hans-Ulrich; Scherer, Bernadette Tetrahedron Letters, 1980 , vol. 21, p. 4259 - 4262]
[Fehr, Charles; Galindo, Jose Journal of Organic Chemistry, 1988 , vol. 53, # 8 p. 1828 - 1830]
Total synthesis of dolabelide C: a phosphate-mediated approach
[Kawanami, Yasuhiro; Dainobu, Yuichiro; Inanaga, Junji; Katsuki, Tsutomu; Yamaguchi, Masaru Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 3 p. 943 - 944]