Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide
Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide
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DOI：
10.1016/j.tetlet.2010.07.040
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发表时间：
2010-09-15
影响因子：
1.8
通讯作者：
Yamaguchi, Masahiko
中科院分区：
文献类型：
--
作者：
Arisawa, Mieko;Yamaguchi, Masahiko
过渡金属配合物以高产率催化醇和酚与四烷基二硫化膦的二烷基硫代膦化反应。苯酚在RhH(PPh(3))(4)和1,2-双(二甲基膦)乙烷存在下在THF回流下反应，醇与Pd(OAc)(2)和1,2-双(二苯基膦)苯在氯苯回流下反应。在这些条件下，伯醇比仲醇反应更快，并且受保护的酪氨酸和丝氨酸被硫膦基化，且外消旋作用最小。二氧化四苯基二膦也发生P-O键形成反应。 (C) 2010 年，爱思唯尔有限公司出版。
Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh(3))(4) and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)(2) and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction. (C) 2010 Published by Elsevier Ltd.