Cu(Ⅰ)-Catalyzed Three Component Reaction Of Terminal Alkynes, Diazoacetamides And Isatin Derived N-Boc Ketoimines

This dissertation mainly introduces a copper(I) salt catalyzed, novel three-component reaction of terminal alkynes, diazoacetamides and isatin derived N-Boc ketoimines.Diazo compound takes a siganificant position in organic synthetic methodology. For its high activity and abundantly varietable reaction properties, diazo compound has been involved in different reactions when treated with corresponding metal catalysts. Multi-component reaction (MCRs), with its high atom economy and step economy, make the synthesis of complex compounds with diversed functional groups from commercial available material more efficient and convenient.Herein, we present a kind of reaction that taking advantage of the high activity of alkyl copper(I) intermediates formed from terminal alkynes and diazoacetamides,then use the isatin derived N-Boc ketoimines as elctronphlic reagents to trap them. Based on the primary experiments, we found several imine structure compounds can trap the intermediates, so after screening of a series of starting materials, we chose terminal alkynes, diazoacetamides and isatin derived N-Boc ketoimines as starting materials. Then we screen the catalysts and solvents to ascertain the standard reaction condition for improving the diastereoselectivity; finally we test a series of starting materials with different substitude groups to detecting the substitutents’electronic and steric effect on the reaction and expand the range of starting material.And we futher investigate the reaction mechanism through the control experiments to exlude the possibility that terminal alkynes and diazoacetamides form the insertion products which further reacts with the imines to afford the final product. We claim the reaction discussed in this dissertation is proved to be a one step trapping three-component reaction rather than a two step but one-pot cascade reaction.