Diazocarbonyl intermolecular 1,3-dipolar

An intermolecular 1,3-dipolar cycloaddition of diazocarbonyl compounds with alkynes was developed by using an InCl3-catalyzed cycloaddition in water. The reaction was found to proceed by a domino 1,3-dipolar cycloaddition-hydrogen (alkyl or aryl) migration (Eq. 12.68).146 The reaction is applicable to various a-diazocarbonyl compounds and alkynes with a carbonyl group at the neighboring position, and the success of the reaction was rationalized by decreasing the HOMO-LUMO of the reaction. 

The 1,3-dipolar cycloaddition of the diazocarbonyl compound 56 with heterocyclic compounds, namely indoles, has been studied by Muthusamy and co-workers [86,87]. Intermolecular cycloaddition of the fused five-membered... 

Li etal. reported the first intermolecular 1,3-dipolar cycloaddition of diazocarbonyl compounds with alkynes, using InCk as catalyst and carrying out the reaction in water [197] (Figure 8.87). Two products were observed from the reaction of a-diazoarylacetates, and the authors had proposed 1,3- or 1,5-shifts ofthe functional... 

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