A modular, air-stable nickel precatalyst

Jason D. Shields; Erin E. Gray; Abigail G. Doyle

doi:10.1021/acs.orglett.5b00766

A modular, air-stable nickel precatalyst

Jason D. Shields, Erin E. Gray, Abigail G. Doyle

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92 Scopus citations

Abstract

The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono- and bidentate phosphines, diimines, and N-heterocyclic carbenes. Preliminary mechanistic studies are also reported, which suggest that [(TMEDA)Ni(o-tolyl)Cl] can activate by either a Ni-B or Ni-Ni transmetalation event, depending on the reaction conditions.

Original language	English (US)
Pages (from-to)	2166-2169
Number of pages	4
Journal	Organic letters
Volume	17
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.5b00766
State	Published - May 1 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5b00766

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title = "A modular, air-stable nickel precatalyst",

abstract = "The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono- and bidentate phosphines, diimines, and N-heterocyclic carbenes. Preliminary mechanistic studies are also reported, which suggest that [(TMEDA)Ni(o-tolyl)Cl] can activate by either a Ni-B or Ni-Ni transmetalation event, depending on the reaction conditions.",

author = "Shields, {Jason D.} and Gray, {Erin E.} and Doyle, {Abigail G.}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.orglett.5b00766",

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AU - Shields, Jason D.

AU - Gray, Erin E.

AU - Doyle, Abigail G.

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N2 - The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono- and bidentate phosphines, diimines, and N-heterocyclic carbenes. Preliminary mechanistic studies are also reported, which suggest that [(TMEDA)Ni(o-tolyl)Cl] can activate by either a Ni-B or Ni-Ni transmetalation event, depending on the reaction conditions.

AB - The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono- and bidentate phosphines, diimines, and N-heterocyclic carbenes. Preliminary mechanistic studies are also reported, which suggest that [(TMEDA)Ni(o-tolyl)Cl] can activate by either a Ni-B or Ni-Ni transmetalation event, depending on the reaction conditions.

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SP - 2166

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

A modular, air-stable nickel precatalyst

Abstract

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