volume 36 issue 8 pages 1662-1672

Oxidative addition of aryl electrophiles to a prototypical nickel(0) complex: mechanism and structure/reactivity relationships

Publication typeJournal Article
Publication date2017-04-06
scimago Q2
wos Q1
SJR0.676
CiteScore5.1
Impact factor2.9
ISSN02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Detailed kinetic studies of the reaction of a model Ni0 complex with a range of aryl electrophiles have been conducted. The reactions proceed via a fast ligand exchange pre-equilibrium, followed by oxidative addition to produce either [NiIX(dppf)] (and biaryl) or [NiII(Ar)X(dppf)]; the ortho substituent of the aryl halide determines selectivity between these possibilities. A reactivity scale is presented in which a range of substrates is quantitatively ranked in order of the rate at which they undergo oxidative addition. The rate of oxidative addition is loosely correlated to conversion in prototypical cross-coupling reactions. Substrates that lead to NiI products in kinetic experiments produce more homocoupling products under catalytic conditions.
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Bajo S. et al. Oxidative addition of aryl electrophiles to a prototypical nickel(0) complex: mechanism and structure/reactivity relationships // Organometallics. 2017. Vol. 36. No. 8. pp. 1662-1672.
GOST all authors (up to 50) Copy
Bajo S., Laidlaw G., Kennedy M. R., Sproules S., Nelson D. J. Oxidative addition of aryl electrophiles to a prototypical nickel(0) complex: mechanism and structure/reactivity relationships // Organometallics. 2017. Vol. 36. No. 8. pp. 1662-1672.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.organomet.7b00208
UR - https://doi.org/10.1021/acs.organomet.7b00208
TI - Oxidative addition of aryl electrophiles to a prototypical nickel(0) complex: mechanism and structure/reactivity relationships
T2 - Organometallics
AU - Bajo, Sonia
AU - Laidlaw, Gillian
AU - Kennedy, M R
AU - Sproules, Stephen
AU - Nelson, D J
PY - 2017
DA - 2017/04/06
PB - American Chemical Society (ACS)
SP - 1662-1672
IS - 8
VL - 36
SN - 0276-7333
SN - 1520-6041
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Bajo,
author = {Sonia Bajo and Gillian Laidlaw and M R Kennedy and Stephen Sproules and D J Nelson},
title = {Oxidative addition of aryl electrophiles to a prototypical nickel(0) complex: mechanism and structure/reactivity relationships},
journal = {Organometallics},
year = {2017},
volume = {36},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.organomet.7b00208},
number = {8},
pages = {1662--1672},
doi = {10.1021/acs.organomet.7b00208}
}
MLA
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MLA Copy
Bajo, Sonia, et al. “Oxidative addition of aryl electrophiles to a prototypical nickel(0) complex: mechanism and structure/reactivity relationships.” Organometallics, vol. 36, no. 8, Apr. 2017, pp. 1662-1672. https://doi.org/10.1021/acs.organomet.7b00208.