Study On The Pallidium-catalyzed Cyclization And Iodine-mediated Electrophilic Cyclization Of Arylalkyne

The cyclization based on alkyne is one of the hottest research topics in organic synthetic chemistry, and it has been widely applied in many frontier areas such as design and synthesis of novel fluorescent materials and medical molecules, etc. In this thesis, the research background of palladium-catalyzed cyclization of alkyne and the iodine-mediated electronphilic cyclization of alkyne is reviewed, and the details of my study are listed as follows:1. Phenalenone derivatives were synthesized via palladium catalyzed bicyclization of1,8-diiodonaphthalene and tertiary propargylic alcohols in an one-pot reaction, the activations of sp,sp2and sp3C-H bonds were included in this reaction. Moreover, the resulting phenalenones could be successfully applied as a potential fluorescent chemosensor for fluoride anion with high sensitivity and selectivity,(see Section1, Chapter2in this thesis)2.8H-Acenaphtho[1,2-c]pyrrole derivatives could be successfully constructed from1,8-diarenynyl naphthalenes and amines. The reaction was conducted under air atmosphere, PdCl2as catalyst and DMSO as reaction solvent. Moreover, the resulting8H-Acenaphtho[1,2-c]pyrroles could be applied as a potential fluorescent chemosensor for trace explosive detection,(see Section2, Chapter2in this thesis)3. β-Dialkylaminonaphthalenes and indenes could be effectively constructed from o-haloacetophenones and terminal alkynes under the control of the Pd catalysts and reaction solvents. Moreover, the β-dialkylaminonaphthalenes could be applied as a potential fluorescent chemosensor for environmental acidity (see Section3, Chapter2in this thesis)4.2,3-Diarylindone and pentaarylpyrrole were respectively constructed from diarylacetylene and arylamine effectively via the control of the reaction solvent in the presence of palladium (Ⅱ) chloride,(see Section4, Chapter2in this thesis)5. Four different types of fused arenes, including fluoranthene, indeno[2,1-a] phenalene,8H-cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene were easily and efficiently constructed via iodine-mediated electrophilic cyclizations of different1,8-dialkynyl naphthalene derivatives in a special solvent,(see Chapter3in this thesis)...