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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

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The design and synthesis of a novel organophosphorus compound containing the structure of both β-amino acid and β-aminophosphonate

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Chinese Chemical Letters 2010年第7期21卷 810-812页

作者： Han Bing Teng College of Chemical Engineering Wuhan University of TechnologyWuhan 430070China

A novel organophosphorus compound containing the structure of bothβ-amino acid andβ-aminophosphonate is designed and *** reaction with P（OEt）_3,the N-Boc protected iodide 3 cannot provide the desired product but 2-oxazolidinone 4 because of the neighboring-group participation of the Boc *** avoid the intramolecular participation of the carbamates,the Ts protecting group is employed and the Ts-protected iodide 5 affords the target product successfully.

关键词： β-Amino acid β-Aminophosphonate Neighboring-group participation arbuzov reaction Amino-protecting group

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