Preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole by a new type of oxidation-reduction condensation using aryl diphenylphosphinite and benzoquinone derivatives

被引:10
作者
Kuroda, Kiichi [1 ]
Hayashi, Yujiro [1 ]
Mukaiyama, Teruaki [2 ]
机构
[1] Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
[2] Kitasato Inst, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
关键词
D O I
10.1246/cl.2008.592
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for the preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and 2,6-dimethoxy-1,4-benzoquinone is described. In this reaction, the chiral alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configurations under mild and neutral conditions.
引用
收藏
页码:592 / 593
页数:2
相关论文
共 21 条
[1]   An efficient method for the preparation of monoalkylated sulfonamides from unsubstituted sulfonamides and alkyl diphenylphosphinites by oxidation-reduction condensation using trimethylsilylmethyl azide [J].
Aoki, H ;
Kuroda, K ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (09) :1266-1267
[2]   Synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones [J].
Baird, CP ;
Rayner, CM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (12) :1973-2003
[3]   The mitsunobu reaction: Origin, mechanism, improvements, and applications [J].
But, Tracy Yuen Sze ;
Toy, Patrick H. .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) :1340-1355
[4]   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 [J].
Ikegai, K ;
Pluempanupat, W ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (05) :638-639
[5]   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 [J].
Ikegai, Kazuhiro ;
Pluempanupat, Wanchai ;
Mukaiyama, Teruaki .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2006, 79 (05) :780-790
[6]   A convenient method for the preparation of alkyl aryl sulfides from alcohols and (chloromethylene)dimethylammonium chloride [J].
Kawano, Y ;
Kaneko, N ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (12) :1612-1613
[7]   HIGH-PRESSURE ORGANIC-CHEMISTRY .13. HIGH PRESSURE-PROMOTED TRANSFORMATION OF ALCOHOLS INTO THE CORRESPONDING PHENYLSULFIDES WITH BU3P-PHSSPH [J].
KOTSUKI, H ;
MATSUMOTO, K ;
NISHIZAWA, H .
TETRAHEDRON LETTERS, 1991, 32 (33) :4155-4158
[8]   Conversion of tertiary alcohols to tert-alkyl azides by way of quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites [J].
Kuroda, Kiichi ;
Hayashi, Yujiro ;
Mukaiyama, Teruaki .
TETRAHEDRON, 2007, 63 (27) :6358-6364
[9]   Cyanation of alcohols with diethyl cyanophosphonate and 2,6-dimethyl-1,4-benzoquinone by a new type of oxidation-reduction condensation [J].
Masutani, Kouta ;
Minowa, Tomofumi ;
Hagiwara, Yoshiaki ;
Mukaiyama, Teruaki .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2006, 79 (07) :1106-1117
[10]   New methods for carbon-nitrogen, carbon-sulfur, and carbon-carbon bond formations by quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites [J].
Mukaiyama, T ;
Ikegai, K ;
Aoki, H ;
Pluempanupat, W ;
Masutani, K .
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2005, 81 (04) :103-109