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C-H…X-C bonds in alkyl halides drive reverse selectivities in confined spaces

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Chinese Chemical Letters 2023年第5期34卷 237-240页

作者： Manuel Petroselli Yong-Qing Chen Ming-Kai Zhao Julius Rebek Jr. Yang Yu Center for Supramolecular Chemistry and Catalysis and Department of Chemistry College of ScienceShanghai UniversityShanghai 200444China Skaggs Institute for Chemical Biology and Department of Chemistry The Scripps Research InstituteLa JollaCA 92037United States

Binding of non-activated alkyl halides(2-20)in water-soluble cavitand(1)through supramolecular forces is here reported,with emphasis on the role of size and polarizability of the halogen atom in the formation of intramolecular C-H hydrogen bonds in confined *** reverse affinity in water(RIalkyl halides in dynamic open-ended *** bindings and theoretical calculations confirm the unusual selectivity and the presence of C-H hydrogen bonds in non-activated systems for the first time,pointing out the importance and effect of subtle forces on molecular recognition in confined spaces.

关键词： Water-soluble cavitand Host-guest complex Molecular recognition C-H hydrogen bond alkyl halides

Nickel-catalyzed umpolung C-S radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides

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Chinese Chemical Letters 2023年第11期34卷 137-142页

作者： Yu-Zhong Yang Gui-Fen Lv Ming Hu Yang Li Jin-Heng Li Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle Nanchang Hangkong UniversityNanchang 330063China State Key Laboratory Base of Eco-Chemical Engineering College of Chemical EngineeringQingdao University of Science and TechnologyQingdao 266042China State Key Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhou 730000China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiang 453007China

A new cooperative nickel reductive catalysis and N,N-dimethylformamide-mediated strategy for umpolung C–S radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides to produce alkyl aryl thioethers is described. This reaction features excellent selectivity, wide functionality tolerance, broad substrate scope, and facile late-stage modification of biologically relevant *** studies recognize initial generation of an amidyl radical anion via thermoinduced reduction of DMF with Sn, followed by umpolung reduction and single electron transfer of the nucleophilic sulfonyl moiety to form a sulphydryl radical and engage the Ni^(0)/Ni^(Ⅰ)/Ni^(Ⅲ)/Ni^(I) catalytic cycle.

关键词： Nickel Radical Reductive cross coupling S-(Trifluoromethyl)arylsulfonothioates alkyl halides alkyl aryl thioethers

Radical Arbuzov Reaction

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CCS Chemistry 2024年第5期6卷 1312-1323页

作者： Linxiang Chai Jian Wang Jimin Yang Junyue Yin Zhuyong Zhang Yulu Cheng Lin Zhu Xiao-Song Xue Chaozhong Li Department of Chemistry University of Science and Technology of ChinaHefeiAnhui 230026 Shanghai Institute of Organic Chemistry Chinese Academy of SciencesShanghai 200032

The Arbuzov reaction(also known as the Michaelis–Arbuzov reaction)is one of the most fundamental transformations in organic chemistry and has been extensively used for the synthesis of organophosphorus compounds for over a ***,the reaction generally requires an elevated temperature and is applicable mainly to primary alkyl halides with poor functional group *** report herein a radical alternative to the conventional nucleophilic substitution ***,new radical phosphonylation reagents,9-fluorenyl o-phenylene phosphite and benzhydryl o-phenylene phosphite,have been developed for this *** photoredox-catalyzed reaction of a wide range of alkyl bromides or iodides with 9-fluorenyl(or benzhydryl)o-phenylene phosphite followed by workup with methanol(or ethanol)provides the corresponding dimethyl(or diethyl)alkylphosphonates in satisfactory yields at room temperature under mild *** method is applicable to primary,secondary,and even tertiary alkyl iodides and bromides and exhibits an excellent functional group tolerance,thereby enabling the late-stage modification of complex molecules and rapid synthesis of phosphonate-containing natural products and drug molecules.A mechanism involving the formation and subsequentβ-scission of phosphoranyl radicals is proposed.

关键词： Arbuzov reaction radicals phosphonylation photoredox catalysis alkyl halides

Nucleophilic Trifluoromethylthiolation of alkyl Chlorides, Bromides and Tosylates

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Chinese Journal of Chemistry 2016年第5期34卷 495-504页

作者： Chunfa Xu Qingyun Chen Qilong Shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chem~try Shanghai 200032 China

A direct nucleophilic trifluoromethylthiolation of alkyl chlorides, bromides and tosylates with AgSCF3 was de- scribed. It was found that the presence of nBu4NI or a combination of nBu4NI/nBu4NBr significantly enhanced the reaction rates. The reaction conditions were mild, thus allowing the tolerance of a variety of functional groups.

关键词： trifluoromethylthiolation nucleophilic fluorine alkyl halides

A Novel Method of Preparing Unsymmetrical Thioether from Disulfides

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Chinese Chemical Letters 2004年第10期15卷 1143-1145页

作者： JingXingDU RenWeiZHENG HongYunGUO LiChunKONG DepartmentofChemistry ZhejiangNormalUniversityJinhua321004

The disulfides reacted with zinc in DMF, followed by alkyl halides, giving unsymmetrical thioether in excellent yields. This reaction takes place under mild and neutral conditions.

关键词： Unsymmetrical thioethers zinc alkyl halides disulfides.

Reductive Cleavage of the Te-Te Bond in Diphenyl Ditelluride by the Sm/CrCl_3(cat.) System: Preparation of Telluroesters and Unsymmetrical Phenyltellurides

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Chinese Journal of Chemistry 2002年第2期20卷 202-206页

作者：刘运奎张永敏 DepartmentofChemistry，ZhejiangUniversity HangzhouZhejiang310028China

The reduction of diphenyl ditelluride by the Sm/CrCl_3(cat.) system led to atelluride anion. This species reacted with acid chlorides, alkyl halides, and α,β-unsaturatedenoates or α,β-unsaturated ene nitriles to afford telluroesters and unsymniet-ricalphenyltellurides, respectively, in moderate to good yields under mild and neutral conditions.

关键词： diphenyl ditelluride samarium/chromium(Ⅲ) chloride(cat.) system acidchlorides alkyl halides α,β-unsatu-rated enoates α,β-unsaturated ene nitriles telluroesters unsym-metrical phenyltelluride

An Efficient and Novel Synthesis of Carbamate Esters from the Coupling of Amines, halides and Carbon Dioxide in the Presence of Basic Resin

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Chinese Chemical Letters 2006年第10期17卷 1309-1312页

作者： Devdutt CHATURVEDI Nisha MISHRA Virendra MISHRA Medicinal & Process Chemistry Division Central Drug Research Institute Lucknow-226001 U. P. India Synthetic Research Lab Department of Chemistry B. S. A. College Mathura-281004 U. P. India

A convenient, efficient, one-pot, novel process has been developed for the synthesis of carbamates from corresponding alkyl halides and amines using basic resin/CO2 system.

关键词： Basic resin (Ambedite IRA 400) alkyl halides carbon dioxide amines carbamates.