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

doi:10.1016/j.tet.2007.11.031

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

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

27 Citations (SciVal)

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 language	English
Pages (from-to)	681-687
Number of pages	7
Journal	Tetrahedron
Volume	64
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2007.11.031
Publication status	Published - 2008

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10.1016/j.tet.2007.11.031

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title = "Negishi cross-coupling reactions of alpha-amino acid-derived organozinc reagents and aromatic bromides",

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.",

author = "Oswald, \{C L\} and T Carrillo-Marquez and Lorenzo Caggiano and Jackson, \{R F W\}",

year = "2008",

doi = "10.1016/j.tet.2007.11.031",

language = "English",

volume = "64",

pages = "681--687",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

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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 - https://www.scopus.com/pages/publications/36849069922

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

SN - 0040-4020

VL - 64

SP - 681

EP - 687

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

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

Abstract

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