Conversion of alcohols to alkyl aryl sulfides by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite
Preparation of alkyl aryl sulfides from alcohols and arenethiols such as 2-sulfanyl-1,3-benzothiazole (BtzSH) is described by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite (PhOPPh 2) and benzoquinone derivatives or azide compounds. This reaction proceeds under mild and neutral conditions and is applicable to the thioetherification of various alcohols in which the chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configuration.
Stereospecific C-S bond formation from chiral tertiary alcohols by quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites and its application to the synthesis of a chiral tertiary thiol
Oxidation-reduction condensation between 2-sulfanyl-1,3-benzothiazole (Btz-SH) and the alkyl diphenylphosphinites 1, prepared from tertiary alcohols, proceeded smoothly in the presence of 2,6-di-t-butyl-1,4-benzoquinone (DBBQ) and the corresponding S-alky
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 ClPPhs