Catalytic Allylation of Hypophosphorous Acid and H-Phosphinic Acids with Primary Allylic Amines

被引：22

作者：

Wu, Xue-Song ^{[1
]}

Zhou, Meng-Guang ^{[1
]}

Chen, Yan ^{[1
]}

Tian, Shi-Kai ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 06期

基金：

中国国家自然科学基金;

关键词：

allylation; amines; H-phosphinic acids; hypophosphorous acid; palladium; N-BENZYLIC SULFONAMIDES; CARBON BOND FORMATION; DEHYDRATIVE ALLYLATION; COUPLING REACTIONS; CLEAVAGE; ALKYLATION; NUCLEOPHILES; NITROGEN; ALLYLAMINES; DERIVATIVES;

D O I：

10.1002/ajoc.201402050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Primary allylic amines serve as suitable allylic electrophiles for the allylation reactions of hypophosphorous acid and H-phosphinic acids. In the presence of tris(dibenzylideneacetone)dipalladium(0) ([Pd-2(dba)(3)], 0.1 mol %) and Xantphos (0.2 mol %), aqueous hypophos-phorous acid was allylated by alpha-unbranched primary allylic amines in a highly regioselective fashion to give structurally diverse allylic H-phosphinic acids in good to excellent yields with exclusive E selectivity. Moreover, increasing the catalyst loading to 1 mol % and adding aqueous phosphoric acid (1.2 equiv.) permitted the allylation of H-phosphinic acids with alpha-unbranched primary allylic amines to proceed to give disubstituted phosphinic acids in good to excellent yields.

引用

页码：711 / 714

页数：4

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