Bisphosphine-Ligated Nickel Pre-catalysts in C(sp2)-N Cross-Couplings of Aryl Chlorides: A Comparison of Nickel(I) and Nickel(II)

被引：44
作者：
Lavoie, Christopher M. [1 ]
McDonald, Robert [2 ]
Johnson, Erin R. [1 ]
Stradiotto, Mark [1 ]
机构：
[1] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4R2, Canada
[2] Univ Alberta, Dept Chem, Xray Crystallog Lab, Edmonton, AB T6G 2G2, Canada
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 17期
基金：
加拿大自然科学与工程研究理事会;
关键词：
C-N cross-coupling; density functional theory (DFT); ligand design; mechanism; nickel; AMINATION; PALLADIUM; LIGAND; TRIFLUOROMETHYLTHIOLATION; PRECATALYSTS; MECHANISM; BROMIDES; HALIDES; ROLES;
D O I：
10.1002/adsc.201700672
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The influence of ancillary ligand and nickel oxidation state in the nickel-catalyzed C(sp(2))-N cross-coupling of aryl chlorides is examined by use of experimental and DFT methods for the first time, focusing on (L) NiCl and (L) Ni(o-tolyl) Cl pre-catalysts (PAd-DalPhos, L1; dppf, L2). Whereas Ni(II) pre-catalysts generally out-performed Ni(I) species in our study, the viability and in some cases superiority of Ni(I) pre-catalysts in challenging aminations is established. Computational analyses support the viability of Ni(0)/Ni(II) cycles featuring rate-limiting CN reductive elimination, as well as parallel Ni(I)/Ni(III) mechanisms involving rate-limiting C-Cl oxidative addition.
引用
收藏
页码：2972 / 2980
页数：9
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