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Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation
2024-06-01
发表期刊ORGANIC CHEMISTRY FRONTIERS (IF:4.6[JCR-2023],4.3[5-Year])
ISSN2052-4129
EISSN2052-4129
卷号11期号:16页码:4502-4507
发表状态已发表
DOI10.1039/d4qo00863d
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.

关键词Alkylphosphonate Dihydropyridines Facile synthesis Fluorenyl Late stage Naturally occurring Phosphonylations Photo-induced Tetrakis Triethylamines
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收录类别SCI ; EI
语种英语
资助项目National Natural Science Foundation of China[
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:001258294500001
出版者ROYAL SOC CHEMISTRY
EI入藏号20242716599259
EI主题词Positive ions
原始文献类型Article in Press
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文献类型期刊论文
条目标识符https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/401424
专题物质科学与技术学院
物质科学与技术学院_特聘教授组_李超忠组
物质科学与技术学院_硕士生
物质科学与技术学院_博士生
通讯作者Zhu, Lin
作者单位
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
第一作者单位物质科学与技术学院
第一作者的第一单位物质科学与技术学院
推荐引用方式
GB/T 7714
Zhang, Huan,Cui, Zhonghe,Wang, Jian,et al. Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation[J]. ORGANIC CHEMISTRY FRONTIERS,2024,11(16):4502-4507.
APA Zhang, Huan,Cui, Zhonghe,Wang, Jian,Zhu, Lin,&Li, Chaozhong.(2024).Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation.ORGANIC CHEMISTRY FRONTIERS,11(16),4502-4507.
MLA Zhang, Huan,et al."Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation".ORGANIC CHEMISTRY FRONTIERS 11.16(2024):4502-4507.
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