화학공학소재연구정보센터
Chemistry Letters, Vol.34, No.5, 638-639, 2005
Preparation of tert-alkyl aryl sulfides from tert-alcohols via quinone-mediated oxidation-reduction condensation between tert-alkyl diphenylphosphinites and 2-sulfanyl-1,3-benzothiazole
A convenient two-step procedure for the construction of sulfur-containing quaternary centers from tert-alcohols involving chiral ones is established. tert-Alkyl diphenylphosphinites 1 were easily prepared in excellent yields from tert-alcohols and ClPPh2 by the combined use of Et3N and a catalytic amount of DMAP. Subsequent condensation of I with thiol 3 smoothly proceeded in the presence of quinone 2d to afford the corresponding tert-alkyl sulfides 4 in good to high yields via S(N)2 displacement. Removal of benzothiazol-2-yl group of (R)-4j was achieved with LiAlH4 to afford the desired chiral thiol (R)-5 in high yield.