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

Reference:

Oswald, C. L., Carrillo-Marquez, T., Caggiano, L. and Jackson, R. F. W., 2008. Negishi cross-coupling reactions of alpha-amino acid-derived organozinc reagents and aromatic bromides. Tetrahedron, 64 (4), pp. 681-687.

Related documents:

Official URL:

http://dx.doi.org/10.1016/j.tet.2007.11.031

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.

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