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NBS‐Promoted Sulfenylation of Sulfinates with Disulfides Leading to Unsymmetrical or Symmetrical Thiosulfonates
Author(s) -
Liang Gaigai,
Liu Miaochang,
Chen Jiuxi,
Ding Jinchang,
Gao Wenxia,
Wu Huayue
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200028
Subject(s) - chemistry , succinimide , combinatorial chemistry , functional group , medicinal chemistry , organic chemistry , polymer
Abstract A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS‐promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom‐economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disul?des generating N ‐(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed.