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Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-06-25 , DOI: 10.1039/d4qo00863d
Huan Zhang 1 , Zhonghe Cui 1 , Jian Wang 2 , Lin Zhu 2 , Chaozhong Li 1, 2
Affiliation  

Here, an unprecedented formal deformylative phosphonylation is disclosed. Under the catalysis of 1 mol% 1,2,3,5-tetrakis(diphenylamino)-4,6-dicyanobenzene (4DPAIPN) and in the presence of 200 mol% triethylamine as an additive, 4-alkyl-1,4-dihydropyridines (DHPs), derived from aldehydes, smoothly underwent phosphonylation with 9-fluorenyl o-phenylene phosphite, allowing facile synthesis of alkylphosphonates. This strategy is applicable to primary, secondary, and even tertiary DHPs and exhibits a broad substrate scope and excellent functional group tolerance, thereby enabling the late-stage phosphonylation of a series of naturally-occurring bioactive and biorelevant molecules.

中文翻译:


通过光诱导形式去酰基膦酰化从 4-烷基-1,4-二氢吡啶轻松合成烷基膦酸酯



在此,公开了前所未有的形式去酰基磷酸化。在1 mol% 1,2,3,5-四(二苯氨基)-4,6-二氰基苯(4DPAIPN)催化下,200 mol%三乙胺作为添加剂存在下,生成4-烷基-1,4-二氢吡啶衍生自醛的 DHP(DHP)可以顺利地与 9-芴基邻亚苯基亚磷酸酯进行膦酰化,从而可以轻松合成烷基膦酸酯。该策略适用于一级、二级甚至三级DHP,并表现出广泛的底物范围和优异的官能团耐受性,从而能够实现一系列天然存在的生物活性和生物相关分子的后期磷酸化。
更新日期:2024-06-28
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