Iron(I) in Negishi Cross-Coupling Reactions

Christopher J. Adams; Robin B. Bedford; Emma Carter; Nicholas J. Gower; Mairi F. Haddow; Jeremy N. Harvey; Michael Huwe; M. Angeles Cartes; Stephen M. Mansell; Carla Mendoza; Damien M. Murphy; Emily C. Neeve; Joshua Nunn

doi:10.1021/ja303250t

Iron(I) in Negishi Cross-Coupling Reactions

Christopher J. Adams, Robin B. Bedford, Emma Carter, Nicholas J. Gower, Mairi F. Haddow, Jeremy N. Harvey, Michael Huwe, M. Angeles Cartes, Stephen M. Mansell, Carla Mendoza, Damien M. Murphy, Emily C. Neeve, Joshua Nunn

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

161 Citations (Scopus)

Abstract

Herein we demonstrate both the importance of Fe(I) in Negishi cross-coupling reactions with arylzinc reagents and the isolation of catalytically competent Fe(I) intermediates. These complexes, [FeX-(dpbz)(2)] [X = 4-tolyl (7), Cl (8a), Br (8b); dpbz = 1,2-bis(diphenylphosphino)benzene], were characterized by crystallography and tested for activity in representative reactions. The complexes are low-spin with no significant spin density on the ligands. While complex 8b shows performance consistent with an on-cycle intermediate, it seems that 7 is an off-cycle species.

Original language	English
Pages (from-to)	10333-10336
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	25
DOIs	https://doi.org/10.1021/ja303250t
Publication status	Published - 27 Jun 2012

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title = "Iron(I) in Negishi Cross-Coupling Reactions",

abstract = "Herein we demonstrate both the importance of Fe(I) in Negishi cross-coupling reactions with arylzinc reagents and the isolation of catalytically competent Fe(I) intermediates. These complexes, [FeX-(dpbz)(2)] [X = 4-tolyl (7), Cl (8a), Br (8b); dpbz = 1,2-bis(diphenylphosphino)benzene], were characterized by crystallography and tested for activity in representative reactions. The complexes are low-spin with no significant spin density on the ligands. While complex 8b shows performance consistent with an on-cycle intermediate, it seems that 7 is an off-cycle species.",

author = "Adams, {Christopher J.} and Bedford, {Robin B.} and Emma Carter and Gower, {Nicholas J.} and Haddow, {Mairi F.} and Harvey, {Jeremy N.} and Michael Huwe and {Angeles Cartes}, M. and Mansell, {Stephen M.} and Carla Mendoza and Murphy, {Damien M.} and Neeve, {Emily C.} and Joshua Nunn",

year = "2012",

month = jun,

day = "27",

doi = "10.1021/ja303250t",

language = "English",

volume = "134",

pages = "10333--10336",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Iron(I) in Negishi Cross-Coupling Reactions

AU - Adams, Christopher J.

AU - Bedford, Robin B.

AU - Carter, Emma

AU - Gower, Nicholas J.

AU - Haddow, Mairi F.

AU - Harvey, Jeremy N.

AU - Huwe, Michael

AU - Angeles Cartes, M.

AU - Mansell, Stephen M.

AU - Mendoza, Carla

AU - Murphy, Damien M.

AU - Neeve, Emily C.

AU - Nunn, Joshua

PY - 2012/6/27

Y1 - 2012/6/27

N2 - Herein we demonstrate both the importance of Fe(I) in Negishi cross-coupling reactions with arylzinc reagents and the isolation of catalytically competent Fe(I) intermediates. These complexes, [FeX-(dpbz)(2)] [X = 4-tolyl (7), Cl (8a), Br (8b); dpbz = 1,2-bis(diphenylphosphino)benzene], were characterized by crystallography and tested for activity in representative reactions. The complexes are low-spin with no significant spin density on the ligands. While complex 8b shows performance consistent with an on-cycle intermediate, it seems that 7 is an off-cycle species.

AB - Herein we demonstrate both the importance of Fe(I) in Negishi cross-coupling reactions with arylzinc reagents and the isolation of catalytically competent Fe(I) intermediates. These complexes, [FeX-(dpbz)(2)] [X = 4-tolyl (7), Cl (8a), Br (8b); dpbz = 1,2-bis(diphenylphosphino)benzene], were characterized by crystallography and tested for activity in representative reactions. The complexes are low-spin with no significant spin density on the ligands. While complex 8b shows performance consistent with an on-cycle intermediate, it seems that 7 is an off-cycle species.

UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-84863475543&partnerID=8YFLogxK

U2 - 10.1021/ja303250t

DO - 10.1021/ja303250t

M3 - Article (Academic Journal)

C2 - 22694754

SN - 0002-7863

VL - 134

SP - 10333

EP - 10336

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 25

ER -

Iron(I) in Negishi Cross-Coupling Reactions

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