2014
DOI: 10.1021/om5006353
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Nickel(II) Complexes Containing Bidentate Diarylamido Phosphine Chelates: Kumada Couplings Kinetically Preferred to β-Hydrogen Elimination

Abstract: A series of divalent nickel complexes containing diarylamido phosphine ligands of the type (o-ArNC 6 H 4 PR 2 ) − (1a, Ar = 2,6-C 6 H 3 Me 2 , R = Ph; 1b, Ar = 2,6-C 6 H 3 iPr 2 , R = Ph; 1c, Ar = 2,6-C 6 H 3 Me 2 , R = iPr; 1d, Ar = 2,6-C 6 H 3 iPr 2 , R = iPr) have been prepared and structurally characterized. The dimeric nickel chloride derivatives {[1b−d]Ni(μ-Cl)} 2 (2b−d) were isolated as brick red microcrystals in high yields from the reactions of NiCl 2 (DME) with either Li[1b−d](solv) x or H[1b−d] in t… Show more

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Cited by 25 publications
(17 citation statements)
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“…Overall, the collected data suggests the successful synthesis of a dimeric structure in which two monomers are bound through two bridging chloride atoms in the form [Ni( Ph dpbp)(μ‐Cl)] 2 (B(Ar F ) 4 ) 2 ( 8 ) (Figure ), which is analogous to the [Ni(dtpbe)(μ‐Cl)] 2 (B(Ar F ) 4 ) 2 (dtpbe=1,2‐bis(di‐ tert ‐butylphosphino)ethane) complex that was reported by Hey‐Hawkins and co‐workers . Compound 8 eluded structural characterization by X‐ray crystallography; therefore, the proposed structure was investigated by DFT calculations at the B3LYP/6‐31G** level of theory (Figure ).…”
Section: Resultsmentioning
confidence: 54%
“…Overall, the collected data suggests the successful synthesis of a dimeric structure in which two monomers are bound through two bridging chloride atoms in the form [Ni( Ph dpbp)(μ‐Cl)] 2 (B(Ar F ) 4 ) 2 ( 8 ) (Figure ), which is analogous to the [Ni(dtpbe)(μ‐Cl)] 2 (B(Ar F ) 4 ) 2 (dtpbe=1,2‐bis(di‐ tert ‐butylphosphino)ethane) complex that was reported by Hey‐Hawkins and co‐workers . Compound 8 eluded structural characterization by X‐ray crystallography; therefore, the proposed structure was investigated by DFT calculations at the B3LYP/6‐31G** level of theory (Figure ).…”
Section: Resultsmentioning
confidence: 54%
“…The scarcity of catalytic reactions involving chelating phosphines is somewhat surprising considering the different reactivity relative to monodentate phosphines that chelating phosphines impart. For example, nickel intermediates with chelating phosphines are less likely to undergo β-H elimination side reactions . These intermediates are also crucial for effective stereo- and regiocontrol of products. , Two general methods exist for utilizing chelating phosphines in nickel(0) catalysis.…”
Section: Introductionmentioning
confidence: 99%
“…For example, nickel intermediates with chelating phosphines are less likely to undergo β-H elimination side reactions. 7 These intermediates are also crucial for effective stereo-and regiocontrol of products. 4b,8 Two general methods exist for utilizing chelating phosphines in nickel(0) catalysis.…”
Section: ■ Introductionmentioning
confidence: 99%
“…Synthesis of a P,N Ligand Precursor . The Liang group has previously reported the synthesis of bidentate, phenylene‐bridged anilido phosphine ligands and their coordination chemistry with Ni and Zn . Examples of Cu and Ni complexes supported by similar ligands have also been reported by Peters and Mindiola, respectively.…”
Section: Resultsmentioning
confidence: 94%