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Lewis Base Catalyzed Selenofunctionalization of Alkynes with Acid-Controlled Divergent Chemoselectivity

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Chinese Journal of Chemistry 2024年第14期42卷 1623-1629页

作者： Ling-Ling Chen Ren-Fei Cao Hua Ke Zhi-Min Chen School of Chemistry and Chemical Engineering Shanghai Key Laboratory for Molecular Engineering of Chiral DrugsShanghai Jiao Tong UniversityShanghai200240 China Engineering Technology Research Center for Environmental Protection Materials Pingxiang UniversityPingxiangJiangxi337055 China

Lewis base catalyzed and Brønsted acid controlled chemodivergent electrophilic selenofunctionalizations of alkynes were developed for the first *** selenium-containing tetrasubstituted alkenes were readily obtained in moderate to excellent yields with complete E/Z *** the substrates were 1-ethynyl naphthol derivatives,linear selenium-containing tetrasubstituted alkenes were produced via intermolecular oxygen nucleophilic attack in the absence of acid additive;in contrast,cyclic selenium-containing tetrasubstituted alkenes were generated through intramolecular carbon nucleophilic capture with the addition of Brønsted acid.

关键词： Alkynes electrophilic addition Chemoselectivity Lewis base catalysis Selenofunctionalization

TEMPO-Regulated Regio-and Stereoselective Cross-Dihalogenation with Dual electrophilic X^(+) Reagents

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Chinese Journal of Chemistry 2021年第11期39卷 3004-3010页

作者： Yi Kong Tongxiang Cao Shifa Zhu Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical EngineeringSouth China University of TechnologyGuangzhouGuangdong510640 China

A TEMPO catalyzed cross-dihalogenation reaction was established via redox-regulation of the otherwise complex system of dual electrophilic X+***,the ICl,BrCl,I_(2) and Br_(2) were generated in-situ,which enabled high regio-or stereoselective access to a myriad of iodochlorination,bromochlorination and homo-dihalogenation products with a wide spectrum of *** its mild conditions and operational simplicity,this method could enable wide applications in organic synthesis,which was exemplified by divergent synthesis of two *** mechanistic investigations via radical clock reaction,pinacol ring expansion and Hammett experiments were conducted,which confirmed the intermediacy of halonium *** addition,a dynamic catalytic model based on the versatile catalytic role of TEMPO was proposed to explain the selective outcomes.

关键词： Halogenation Organocatalysis electrophilic addition Redox-regulation Alkynes

State-of-the-Art in electrophilic Trifluoromethylthiolation Reagents

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Chinese Journal of Chemistry 2016年第5期34卷 445-454页

作者： Helene Chachignon Dominique Cahard Normandie UniversitY CNRS UMR 6014 COBRA et FR 3038 Universite de Rouen INSA Rouen. 1 rue Tesniere 76821 Mont Saint-Aignan Cedex France

The trifluoromethylthio group （SCF3） is a fluorine chemotype that has experienced a strong acceleration of in- terest in the recent years. It is particularly true of the construction of new fluorinated architectures by electrophilic trifluoromethylthiolation. The spread of knowledge was already very active in this research domain in the sixties; however, gaseous and highly toxic trifluoromethanesulfenyl chloride （CF3SC1） was the only reagent available at that time. Nowadays, one really can speak of a revival in the field thanks to the rapid development of a wide pano- ply of reagents that are stable and easy to handle. This review provides a historical perspective of the development of shelf-stable electrophilic trifluoromethylthiolation reagents.

关键词： fluorine sulfur electrophilic addition synthetic methods

Synthesis of 3-Methylthioindoles via Intramolecular Cyclization of 2-Alkynylanilines Mediated by DMSO/DA/lSO-d_(6) and SOCI_(2)

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Chinese Journal of Chemistry 2021年第5期39卷 1211-1224页

作者： Xuemin Li Beibei Zhang Jingran Zhang Xi Wang Dongke Zhang Yunfei Du Kang Zhao Tianjin Key Laboratory for Modern Drug Delivery&High-Efficiency School of Pharmaceutical Science and TechnologyTianjin UniversityTianjin 300072China State Key Laboratory of Microbial Technology Institute of Microbiol TechnologyShandong UniversityQingdaoShandong 266237China

The intramolecular cyclization of 2-alkynylanilines mediated by DMSO/SOCI_(2) was found to afford biologically interesting 3-methylthioindoles,which are rarely obtained by the exiting *** could also be replaced with its deuterated counterpart,enabling the method applicable to the construction of indole skeleton bearing a SCD_(3) moiety at its 3-position.

关键词： DMSO electrophilic addition Cyclization 3-Methylthioindoles Synthetic methods

Effect of EtOH on the E-Iodohydroxylation of 1,2-Allenylic Sulfoxides with I_(2)

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Chinese Journal of Chemistry 2004年第9期22卷 990-993页

作者：傅春玲陈国飞邓友前黄宪麻生明 Department of Chemistry Zhejiang UniversityHangzhouZhejiang 310027China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences354 Fenglin LuShanghai 200032China

The E-iodohydroxylation of 1,2-allenylic sulfoxides with I2 in the presence of EtOH afforded 3-phenylsulfinyl- 2-iodo-2(E)-alkenols in good yields and regio/stereo-selectivities under very mild conditions.

关键词： electrophilic addition iodohydroxylation allene sulfoxide