TY - JOUR
T1 - Negishi cross-coupling reactions of alpha-amino acid-derived organozinc reagents and aromatic bromides
AU - Oswald, C L
AU - Carrillo-Marquez, T
AU - Caggiano, Lorenzo
AU - Jackson, R F W
PY - 2008
Y1 - 2008
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=36849069922&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1016/j.tet.2007.11.031
U2 - 10.1016/j.tet.2007.11.031
DO - 10.1016/j.tet.2007.11.031
M3 - Article
VL - 64
SP - 681
EP - 687
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 4
ER -