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Catalytic Allylation of Hypophosphorous Acid and H ‐Phosphinic Acids with Primary Allylic Amines
Author(s) -
Wu XueSong,
Zhou MengGuang,
Chen Yan,
Tian ShiKai
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402050
Subject(s) - allylic rearrangement , chemistry , xantphos , catalysis , regioselectivity , electrophile , organic chemistry , medicinal chemistry , phosphoric acid , selectivity , palladium
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 hypophosphorous acid was allylated by α‐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 α‐unbranched primary allylic amines to proceed to give disubstituted phosphinic acids in good to excellent yields.