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Synthesis of α,β-Unsaturated Diazoketones through the Use of N,N'-Ditosylhydrazine
Alexander R Pelley1, Salman Bagherzadeh1, Jian-Bin Lin2
1Chemistry Department, Memorial University of Newfoundland and Labrador, 45 Arctic Avenue, St. John's, NL A1C 5S7, Canada.
Abstract:
A scalable synthesis of α,β-unsaturated diazoketones has been developed through the reaction of 1-iodoenones with N,N'-ditosylhydrazine. 1-Chloroenones, accessible from aldehydes via a Wittig-type homologation, undergo in situ halide exchange and diazo transfer in a one-pot sequence that minimizes purification and enhances efficiency. This strategy offers practical access to α,β-unsaturated diazoketones, which serve as versatile intermediates for synthesis and reaction discovery. In addition, selective formation of dihydropyridazinones through a 1,4-addition pathway is described.
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