Affiliation:
1. Hainan Institute of East China Normal University State Key Laboratory of Petroleum Molecular & Process Engineering Shanghai Key Laboratory of Green Chemistry and Chemical Processes School of Chemistry and Molecular Engineering East China Normal University Shanghai 200062 P.R. China
2. School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 P.R. China
3. State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 P. R. China
Abstract
AbstractPolysulfides are significant compounds in life science, pharmaceutical science, and materials science. Therefore, polysulfide construction is in great demand. The controllable sequential installation of groups on both ends of a S−S motif faces an enormous challenge owing to the reversible nature of the covalent S−S bond. A library was established with two divergent mask groups for bilateral unsymmetrical disulfurating reagents (R1O−SS−SO2R2). Sequential coupling with preferential activation of the S−SO2 bond (37.6 kcal/mol) and controllable activation of the S−O bond (54.8 kcal/mol) in the presence of the S−S bond (62.0 kcal/mol) enabled successive reactions at each end of the S−S motif to afford unsymmetrical disulfides and trisulfides, even for the cross‐linkage of natural products, pharmaceuticals, peptides, and a protein (bovine serum albumin).
Funder
National Outstanding Youth Science Fund Project of National Natural Science Foundation of China
Science and Technology Commission of Shanghai Municipality
Fundamental Research Funds for Central Universities of the Central South University