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Synthesis of 9-phenol-substituted xanthenes by cascade O-insertion/1,6-conjugate addition of benzyne with ortho-hydroxyphenyl substituted para-quinone methides

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Chinese Chemical Letters 2019年第2期30卷 386-388页

作者： Zhijuan Li Weihua Wang Hui Jian Wenjuan Li Bin Dai Lin He Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan School of Chemistry and Chemical EngineeringShihezi University

The cascade O-insertion/1,6 conjugate addition between benzynes and ortho-hydroxyphenyl substituted para-quinone methides has been reported, affording 9-phenol substituted xanthenes in 49%-84% yields.

关键词： benzyne para-Quinone methides Xanthene Cascade reaction Cycloaddition

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Benzisoxazole core and benzoxazolopyrrolidine via HDDA-derived benzyne with PTIO/DMPO

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Chinese Chemical Letters 2023年第4期34卷 318-321页

作者： Yu Lei Wenjing Zhu Yajuan Zhang Qiong Hu Jie Dong Yimin Hu Key Laboratory of Functional Molecular Solids Ministry of EducationAnhui Laboratory of Molecule-Based MaterialsState Laboratory Cultivation BaseCollege of Chemistry and Materials ScienceAnhui Normal UniversityWuhu 241002China

A novel method for HDDA-derived benzyne trapped by nitrone was developed. This research described a simple and efficient pathway for the synthesis of benzisoxazoles from arynes and PTIO(2-phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl), C-C and C-O bonds were formed in a single step without catalyst under mild conditions. The unexpected cleavage of C-N bond contributed to the formation of isoxazole ring, as indicated by DFT studies. Furthermore, we obtained the structure of benzoxazolopyrrolidine when the trapping agent is DMPO(5,5-dimethyl-1-pyrroline N-oxide).

关键词： Benzisoxazole HDDA reaction benzyne Nitrone Heterocycle

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Nickel-Catalyzed Electroreductive Syntheses of Triphenylenes Using ortho-Dihalobenzene-Derived benzynes

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Chinese Journal of Chemistry 2022年第19期40卷 2335-2344页

作者： Zhao-Ming Li Bin Shuai Cong Ma Ping Fang Tian-Sheng Mei State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling RoadShanghai200032 China

Electrochemical nickel-catalyzed syntheses of triphenylenes by a)reductive trimerization of ortho-dibromobenzenes or ortho-bromoarylsulfurofluoridates,or b)reductive cross-coupling of ortho-dibromobenzenes to 2,2’-diiodobiphenyls,are *** former provides a practical means for the construction of triphenylene derivatives in up to 87%isolated yield at room *** 1,2-dihalo-3-methylbenzenes and related ortho-trisubstituted substrates,trimerizations proceed with high substrate-controlled regioselectivity for the non-C3h symmetric triphenylene isomer.

关键词： Electrochemistry Ni catalysis benzyne Cyclotrimerization Cross coupling

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The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes

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Science China Chemistry 2019年第11期62卷 1425-1438页

作者： Andrew J.Smith Darren L.Poole John A.Murphy Department of Pure and Applied Chemistry University of StrathclydeStrathclydeGlasgow G11XLUnited Kingdom Flexible Discovery Unit GlaxoSmithKline Medicines Research CentreStevenageSG12NYUnited Kingdom

Coupling reactions between haloarenes and arenes(including heteroarenes)that are conducted without added transition metals but in the presence of KOtBu or NaOtBu,have been a topic of great interest since their discovery in *** organic structures act as additives that assist these *** additives are converted into organic electron donors by the butoxide base and this leads to initiation of the coupling reactions,which proceed by radical chain *** review provides an overview of the initiation stages of these reactions.

关键词： organic electron donor potassium tert-butoxide electron transfer base-promoted homolytic aromatic substitution(BHAS) coupling benzyne

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Synthesis of Potential Inhibitiors for Stat-3 Dimerization

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Chinese Journal of Chemistry 2006年第9期24卷 1163-1169页

作者：崔家荣简亚军伍贻康王少萌 State Key Laboratory of Bio-organic and Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China Department of Chemistry Northwest University Xi'an Shaanxi 710069 China Departments of Internal Medicine and Medicinal Chemistry University of Michigan Ann Arbor M148109 USA

Nine bioactive ochromycinone analogues were synthesized through two different types of routes. Some unexpected products were obtained in the photo-induced oxidation. The syntheses disclosed herein complement those in the literature and offer inexpensive access to many of the known intermediates involved, most of which were studied years ago in completely different contexts.

关键词： inhibitor antitumor agent benzyne aromatics angucyclinone

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A Step Beyond the Boundary of Traditional Aryne Chemistry

A Step Beyond the Boundary of Traditional Aryne Chemistry

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中国化学会·第十六届全国有机合成化学学术研讨会

作者：李杨重庆大学

Polysubstituted arene structural motifs broadly exist in numerous natural products, drug molecules, and organic functional materials. How to quickly construct them continues to be one of the themes in organic *** traditional benzyne intermediate can readily assemble vicinal difunctionalized arenes, it has been restricted to accomplish multifunctionalization with this highly active species. Our research focuses on the ways to break the limitation of traditional arene chemistry, which could be achieved via either 1,2-benzdiyne(namely domino aryne) chemistry or cascade simple aryne reaction/C-H functionalization. Meanwhile, we are interested in the discovery of new research maneuvers in aryne chemistry. Along with the development of our aryne multifunctionalization systems, several drug molecules could be prepared as well.

关键词： benzyne aryne cyclohexyne domino reaction polysubstitued arene

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Three-Component Coupling of Alkynes with Alkenes and Organometallic Reagents Catalyzed by Transition Metal Complexes

Three-Component Coupling of Alkynes with Alkenes and Organom...

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13th Asian Chemical Congress

作者： CHENG,Chien-Hong Department of Chemistry National Tsing Hua University Hsinchu 30043

＜正＞Metal-catalyzed domino reactions that involve the coupling of twoπ-components with main group organometallics have become useful methods for assembling complex molecular structures from simple starting *** type of reactions has grown significantly in scope.A similar reaction sequence using arynes as aπ-component would be highly interesting and useful,considering that arynes are generally very reactive,in situ generated and that the reaction would lead to the formation

关键词： nickel-catalyzed benzyne alkene alkyne three-component coupling

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