Negishi cross-coupling reactions of alpha-amino acid-derived organozinc reagents and aromatic bromides

C L Oswald, T Carrillo-Marquez, Lorenzo Caggiano, R F W Jackson

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

The Negishi cross-coupling reaction of organozinc iodides derived from alpha-amino acids with aromatic bromides to give substituted phenylalanine derivatives is described, using either Pd(OAc)(2) or Pd-2(dba)(3) in combination with P(o-Tol)(3) as catalyst in DMF at 50 degrees C. Similar results are obtained using Pd[P'Bu-3](2) as catalyst. The difference in reactivity displayed between aryl iodides and bromides (ArI>ArBr) has been utilised in a short synthesis of an unsymmetrical, orthogonally protected para-phenylene bis-alanine derivative.
Original languageEnglish
Pages (from-to)681-687
Number of pages7
JournalTetrahedron
Volume64
Issue number4
DOIs
Publication statusPublished - 2008

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