Efficient One-Pot Preparation of Methylthio Arylbutadiynes by Double Elimination Protocol

Abstract

A novel and efficient method for preparation of methylthio arylbutadiynes (Ar-C≡C-C≡C-SCH₃) was described, and a series of compounds have been expediently obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. The mechanism was discussed on the basis of trapping and characterization of key intermediates. The results from experiments indicated that the reaction involved the initial nucleophilic addition of MP-S to arylpropargyl aldehydes to produce an intermediate carrying two leaving groups and subsequent double elimination reactions.

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GRAPHICAL ABSTRACT

Keywords:

• Double elimination
• methylthio arylbutadiyne
• one-pot preparation

ACKNOWLEDGMENTS

We are grateful for the financial support from the National Natural Science Foundation of China (No. 21072052), the National Basic Research Program of China (No. 2009CB421601), and Hunan Provincial Science and Technology Department Program (Nos. 2011WK4007, 06FJ4115).

Notes

^a Yield of the isolated product.

^a Yield of the isolated product.

^b Yield based on intermediate 5.