双消除法一锅合成甲硫芳炔化合物

描述了一种方便的合成甲硫芳炔化合物的新方法. 利用亲核硫试剂甲硫甲基苯基砜(methylthiomethyl phenyl sulfone, MP-S)与芳香醛的“一锅反应”, 成功地合成了一系列甲硫芳炔化合物1a～1h．通过对各阶段形成的中间体的分析, 探讨了1的形成机制．实验结果表明, 一锅反应经历了双离去基中间体2的形成和后续的两次消除过程．该方法原料易得, 操作简单, 可得到较好的产率(＞70%). 此外, 反应还具有副产物少、容易分离和纯化的优点．

One-Pot Synthesis of Methylthio Aryl Ethynes by Double Elimination Protocol

A novel method for synthesis of methylthio aryl ethynes was described, and eight compounds 1a～1h were obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and aromatic aldehydes. The mechanism for the formation of 1 was discussed on the basis of trapping and characterization of some important intermediates. The results from experiments indicated that the reaction might involve the initial nucleophilic addition of MP-S to aromatic aldehyde to produce an intermediate 2 carrying two leaving groups, followed by double eliminations using lithium diisopropylamide (LDA) as base to form 1. This method is not only simple, but also does not require a tedious separation of the reaction mixtures because of less by-product.