Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation

被引:2
|
作者
Zhang, Huan [1 ]
Cui, Zhonghe [1 ]
Wang, Jian [2 ]
Zhu, Lin [2 ]
Li, Chaozhong [1 ,2 ]
机构
[1] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Fluorine & Nitrogen Chem & Adv Mat, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 16期
基金
中国国家自然科学基金;
关键词
RADICAL TRAP; 1,4-DIHYDROPYRIDINES; ALKYLATION;
D O I
10.1039/d4qo00863d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4502 / 4507
页数:6
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