Sulfonium ylide formation and subsequent CS bond cleavage of aromatic isopropyl sulfide catalyzed by hemin in aqueous solvent. Issue 23 (7th June 2019)

• Record Type: Journal Article
• Authors: Yan, Xiaojing; Li, Chang; Xu, Xiaofei; He, Quan; Zhao, Xiaoyong; Pan, Yuanjiang
• Is Part Of: Tetrahedron. Volume 75:Issue 23(2019)
• Page Start: 3081
• Page End: 3087
• Publication Date: 2019-06-07
• Subjects: Hemin -- Sulfonium ylide -- CS bond cleavage -- Aqueous catalytic system -- Diazo ester -- Late stage functionalization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.035
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Heme is an abundant and widely existed cofactor for a variety of metalloenzymes, whose broader use is generally impeded by its high instability and poor solubility. Here we report an environment-benign and efficient strategy for the sulfonium ylide formation and subsequent CS bond cleavage of aromatic isopropyl sulfides, which was catalyzed by hemin in assistance of Triton X-100. This aqueous catalytic system exhibited good functional group tolerance to a variety of sulfides and diazo esters. And the reaction mechanism was preliminarily proposed on the basis of designed reactions. Furthermore, the cleavage of CS bond followed by introducing a functional ester group to aromatic sulfides, may potentially be employed for the late stage functionalization (LSF) of organosulfur drug in the future. Graphical abstract: Image 1