| Transition metal-mediated functionalization reactions widely provide effective functional groups in biological macromolecules and unsaturated organic compounds,and can also be used for unsaturated bonds,such as the modification of alkenes and alkynes,and the synthesis of drug molecules,which has great research significance in practical applications.Based on this,I explored and realized the transition metal-mediated acetylation of the non-activated olefin sp~2C-H bond and the acylation of[1.1.1]propellane in the postgraduate stage.It includes the following three parts:Part one:Summarize the research results in the field of various functionalization reactions of non-activated olefin sp~2C-H andbisubstituted or monosubstituted reactions of[1.1.1]propellane,and thus lead to the topic of the paper.Part two:This paper introduces the acetylation of non-activated olefin sp~2C-H bond by 8-aminoquinoline guidance strategy to construct conjugated 1,3-enyne compounds.The reaction carried out alkynylation at the far end of the inactive alkenes to produce conjugated 1,3-enynes with non-enantioselectivity and regioselectivity,which can tolerate a variety of aryl and alkyl substituted alkenes.Under the guidance of 8-aminoquinoline,the operation is simple,the yield is stable,the deprotection and the departure of the guiding group are easy,which complements the existing methods of regioselective production of conjugated 1,3-enynes from non-enantiomers.Part three:A method of free radical acylation of[1.1.1]propellane and aldehyde was proposed.This method uses commercially available,cheap and stable aromatic aldehydes or alkyl aldehydes as the source of acyl radicals.The steps are simple,the conditions are mild,and bicyclo[1.1.1]pentane ketones can be directly synthesized,and has good substrate universality.It can be used for the later modification of bioactive molecules,and bicyclo[1.1.1]pentane ketones can also be used for multifunctional conversion,which is of great significance for drug research. |
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