TBAB-Catalyzed 1,6-Conjugate Sulfonylation of <i>para</i>-Quinone Methides: A Highly Efficient Approach to Unsymmetrical <i>gem</i>-Diarylmethyl Sulfones in Water
Zhang-Qin Liu,
Peng-Sheng You,
Liang-Dong Zhang,
Da-Qing Liu,
Sheng-Shu Liu,
Xiao-Yu Guan
Affiliations
Zhang-Qin Liu
Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
Peng-Sheng You
Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
Liang-Dong Zhang
Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
Da-Qing Liu
Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
Sheng-Shu Liu
Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
Xiao-Yu Guan
Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
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.
