N-Methylimidazole-catalyzed Synthesis of Carbamates from Hydroxamic Acids via the Lossen Rearrangement
Sabesan Yoganathan and Scott J. Miller*
*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States, Email: scott.milleryale.edu
S. Yoganathan, S. J. Miller, Org. Lett., 2013, 15, 602-605.
DOI: 10.1021/ol303424b (free Supporting Information)
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A catalytic amount of N-methylimidazole (NMI) accelerated a mild one-pot synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers.
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