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- Publisher
- Wiley
- Copyright
- Copyright © 2014 Wiley Subscription Services, Inc., A Wiley Company
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201402050
- Publisher site
- See Article on Publisher Site
Abstract
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) ([Pd2(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.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Jun 1, 2014
Keywords: ; ; ; ;