Ni Or Cu-catalyzed C(sp~2)-C(sp~3) Bonds Construction

Transition metal catalyzed C-C bond cross-coupling reaction is regarded as a powerful tool of synthetic chemistry.The past few decades,lots of transition metal catalyzed cross-coupling reaction methods were reported,and widely used in the synthesis-of complex natural molecules.C(sp~2)-C(sp~3)reaction have good application value in the synthesis,the new synthetic method has always been the focus of attention.In this paper,in the first chapter we briefly stated the Copper and Nickel transition metal catalyzed of C(sp~2)-C(sp~3)bond cross-coupling reaction.Organometallic reagents to participate in the cross-coupling reaction mainly includes the following reagents:organic zinc reagent,boron reagents,silicon reagents,zirconium reagents etc.While traditional electrophilic reagents mainly halide and sulfonic acid ester.Recent epoxy and acridine with C(sp~2)negative reagent ring-opening cross-coupling reaction to build C(sp~2)-C(sp~3)bond has attracted a lot of interest.Compared to the traditional halide and sulfonic acid ester halide,epoxy and acridine ring-opening cross-coupling reaction can also bring in alkyl alcohol and alkyl amine.The alkyne with alkyl electrophilic reagent hydrogen-alkylation reaction to build C(sp~2)-C(sp~3)bond attracted the interest of the people.Its advantage is that this reaction does not need to use metal reagent,alkynes are cheap and not sensitive to air and water.In chapter 2,we reported the Cu catalyst aryl boron with epoxide ring opening reaction.Olefins is a kind of important organic molecules,which are widely exists in materials,the pharmaceutical industry.Recently,alkynes with sp~3 electrophilic reagent intermolecular hydrogel-alkylation reaction to build C(sp~2)-C(sp~3)bond reactions respected by people.However,alkynes and sp~3 type electrophilic reagents cross-coupling reaction is very few.The first example is Lalic group reported Cu-catalytic terminal alkynes with C(sp~3)electrophilic reagents reaction.The second example is Hu group reported Fe-catalytic phenyl acetylene and sp~3 type electrophilic reagent reaction.In the third chapter,we choose terminal alkynes with alkyl iodine as the substrate,and reported the first example of terminal alkynes with sp~3 type electrophilic reagents markov selective hydrogen-alkylation reaction.The reaction does not need to use metal reagent and has mild reaction condition.