TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water.

Zhang-Qin Liu, Peng-Sheng You, Liang-Dong Zhang, Da-Qing Liu, Sheng-Shu Liu, Xiao-Yu Guan

Molecules (Basel, Switzerland) 2020 Jan 26

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A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

Citation

Zhang-Qin Liu, Peng-Sheng You, Liang-Dong Zhang, Da-Qing Liu, Sheng-Shu Liu, Xiao-Yu Guan. TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water. Molecules (Basel, Switzerland). 2020 Jan 26;25(3)