1, 6-Conjugate sulfonylation of para-quinone methides: An expedient approach to unsymmetrical gem-diarylmethyl sulfones. Issue 3 (17th January 2019)

• Record Type: Journal Article
• Authors: Guan, Xiao-Yu; Zhang, Liang-Dong; You, Peng-Sheng; Liu, Sheng-Shu; Liu, Zhang-Qin
• Is Part Of: Tetrahedron letters. Volume 60:Issue 3(2019)
• Page Start: 244
• Page End: 247
• Publication Date: 2019-01-17
• Subjects: Sulfonylation -- 1, 6-Conjugated addition -- Diarylmethyl sulfones -- para-Quinone methides -- Sodium arylsulfinates; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.12.023
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A novel sulfonylation of para -quinone methides with sodium arylsulfinates. An inexpensive and efficient synthesis of unsymmetrical gem -diarylmethyl sulfones. High functional group tolerance, and scalability (gram scale). Further transformation of the diarylmethyl sulfones were also demonstrated. Abstract: A novel sulfonylation of para -quinone methides with sodium arylsulfinates has been developed via acetic acid promoted sulfa-Michael addition. This reaction provides an inexpensive and efficient method to synthesize various unsymmetrical diarylmethyl sulfones, displaying the advantages of high atom economy, good functional group tolerance, scalability, and environmentally friendly operation. Derivations of target products are also demonstrated.