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N-S Bond Formation

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In ionic liquids [Bmim][PF6] or [Bmim][BF4], a highly regioselective N-substitution of pyrrole with alkyl halides, sulfonyl chlorides, and benzoyl chloride gave substituted pyrroles in excellent yields. Michael addition of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford N-alkylpyrroles.
Z.-G. Lea, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004, 1951-1954.


N-Trifluoroacetyl arenesulfenamides are effective precursors for the synthesis of unsymmetrical disulfides and sulfenamides.
M. Bao, M. Shimizu, Tetrahedron, 2003, 59, 9655-9659.