Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand

Martinez, Jorge L.; Lee, Wei-Tsung; Pink, Maren; Chen, Chun-Hsing; Smith, Jeremy M.

doi:10.1016/j.poly.2018.09.026

Title: Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand

Abstract

Bis(carbene)borate ligand transfer to the nickel nitrosyl synthon Ni(NO)(PPh₃)₂Br provides the new nickel nitrosyl complex Ph₂B(^tBuIm)₂Ni(NO)(PPh₃). The solid state structure reveals a trigonal pyramidal nickel ion with a very long bond to the apical PPh₃ ligand. The complex reversibly dissociates PPh₃ in solution to afford three-coordinate Ph₂B(^tBuIm)₂Ni(NO), with NMR data providing evidence for PPh₃ binding at low temperatures. Ligand transfer to Ni(PMe₃)₂Cl₂ provides the square planar complex, Ph₂B(^tBuIm)₂Ni(PMe₃)Cl, which shows no evidence for rearranging to the form a homoleptic complex with two bis(carbene)borate ligands. This complex is a suitable synthon for the [Ph₂B(^tBuIm)₂Ni]⁺ fragment, as demonstrated by the synthesis of the π-allyl complex Ph₂B(^tBuIm)₂Ni(η³-C₇H₇). The π-allyl complex reacts with O₂ to provide benzaldehyde and an unstable complex that is tentatively identified as the nickel(II) hydroxide [Ph₂B(^tBuIm)₂Ni(μ-OH)]₂.

Authors:

Martinez, Jorge L. ^[1]; Lee, Wei-Tsung ^[2]; Pink, Maren ^[2]; Chen, Chun-Hsing ^[2]; Smith, Jeremy M. ^[2]

Indiana Univ., Bloomington, IN (United States). Dept. of Chemistry; Loyola Univ. Chicago, Chicago, IL (United States). Dept. of Chemistry and Biochemistry
Indiana Univ., Bloomington, IN (United States). Dept. of Chemistry

Publication Date:: 2018-09-25

Research Org.:: New Mexico State Univ., Las Cruces, NM (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

OSTI Identifier:: 1471492

Alternate Identifier(s):: OSTI ID: 1636409

Grant/Contract Number:: FG02-08ER15996

Resource Type:: Accepted Manuscript

Journal Name:: Polyhedron

Additional Journal Information:: Journal Volume: 156; Journal Issue: 1; Journal ID: ISSN 0277-5387

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Nickel complexes; nitrosyl ligands, NHC complexes, bidentate ligands; dioxygen reactivity

Citation Formats


                    Martinez, Jorge L., Lee, Wei-Tsung, Pink, Maren, Chen, Chun-Hsing, and Smith, Jeremy M.. Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand.  United States: N. p., 2018. 
Web.  https://doi.org/10.1016/j.poly.2018.09.026.

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                    Martinez, Jorge L., Lee, Wei-Tsung, Pink, Maren, Chen, Chun-Hsing, & Smith, Jeremy M.. Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand.  United States.  https://doi.org/10.1016/j.poly.2018.09.026

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                    Martinez, Jorge L., Lee, Wei-Tsung, Pink, Maren, Chen, Chun-Hsing, and Smith, Jeremy M.. Tue .  
"Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand".  United States.  https://doi.org/10.1016/j.poly.2018.09.026.  https://www.osti.gov/servlets/purl/1471492.

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@article{osti_1471492,

  title        = {Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand},

  author       = {Martinez, Jorge L. and Lee, Wei-Tsung and Pink, Maren and Chen, Chun-Hsing and Smith, Jeremy M.},

  abstractNote = {Bis(carbene)borate ligand transfer to the nickel nitrosyl synthon Ni(NO)(PPh3)2Br provides the new nickel nitrosyl complex Ph2B(tBuIm)2Ni(NO)(PPh3). The solid state structure reveals a trigonal pyramidal nickel ion with a very long bond to the apical PPh3 ligand. The complex reversibly dissociates PPh3 in solution to afford three-coordinate Ph2B(tBuIm)2Ni(NO), with NMR data providing evidence for PPh3 binding at low temperatures. Ligand transfer to Ni(PMe3)2Cl2 provides the square planar complex, Ph2B(tBuIm)2Ni(PMe3)Cl, which shows no evidence for rearranging to the form a homoleptic complex with two bis(carbene)borate ligands. This complex is a suitable synthon for the [Ph2B(tBuIm)2Ni]+ fragment, as demonstrated by the synthesis of the π-allyl complex Ph2B(tBuIm)2Ni(η3-C7H7). The π-allyl complex reacts with O2 to provide benzaldehyde and an unstable complex that is tentatively identified as the nickel(II) hydroxide [Ph2B(tBuIm)2Ni(μ-OH)]2.},

  doi          = {10.1016/j.poly.2018.09.026},

  journal      = {Polyhedron},

  number       = 1,

  volume       = 156,

  place        = {United States},

  year         = {2018},

  month        = {9}

}

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Figure 1: Bis(carbene)borate ligands to stabilize homoleptic and heteroleptic iron(II) complexes.

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Works referenced in this record:

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Figures / Tables found in this record:

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Six-coordinate Mn^III complexes are typically high-spin (S = 2), however, the scorpionate ligand, both in its traditional, hydridotris(pyrazolyl)borate form, Tp^- and Tp*^- (the latter with 3,5dimethylpyrazole substituents) and in an aryltris(carbene)borate (i.e. , N -heterocyclic carbene, NHC) form, [Ph(MeIm)₃B]^-, (MeIm = 3-methylimidazole) lead to formation of bis(scorpionate) complexes of Mn^III with spin triplet ground states; three of which were investigated herein: [Tp₂Mn]SbF₆ (1SBF₆), [Tp*₂Mn]SbF₆ (2SBF₆), and [{Ph(MeIm)₃B}₂Mn]CF₃SO₃ (3CF₃SO₃). These trigonally symmetric complexes were studied experimentally by magnetic circular dichroism (MCD) spectroscopy (the propensity of 3 to oxidize to Mn^IV precluded collection of useful MCD data) including variable temperatures and fieldsmore »« less
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Double deprotonation of the salt [Ph₂B(PMe₃)₂][OTf] (1) provides access to a bis(ylide)diphenylborate ligand that is readily transferred in situ to iron(II). Depending on the reaction stoichiometry, both the “ate” complex [Ph₂B(Me₂PCH₂)₂Fe(μ-Cl)₂Li(THF)₂] (2) and the homoleptic complex [Ph₂B(Me₂PCH₂)₂]₂Fe(3) can be prepared from FeCl₂(THF)_1.5. Further reaction of 3 with FeCl₂(THF)1.5 produces the chloride-bridged dimer [Ph₂B(Me₂PCH₂)₂Fe(μ-Cl)2Fe(CH₂PMe₂)₂BPh₂](4). Attempts to reduce or alkylate 4 provide 3 as the only isolable product, likely a consequence of the low steric hindrance of the bis(ylide)diphenylborate ligand. On the other hand, reaction of 4 with the strong field ligand CN^tBu provides the six-coordinate, diamagnetic complex [Ph₂B(Me₂PCH₂)₂Fe(CN^tBu)₄][Cl](5). Electronic structure calculationsmore »« less
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Title: Heteroleptic Nickel Complexes of a Bulky Bis(carbene)borate Ligand

Abstract

Citation Formats

Figures / Tables:

Kinetics, Thermodynamics, and Effect of BPh 3 on Competitive C−C and C−H Bond Activation Reactions in the Interconversion of Allyl Cyanide by [Ni(dippe)] journal, March 2004

Cleavage of Carbon−Carbon Bonds in Alkyl Cyanides Using Nickel(0) journal, August 2004

Solvent Effects and Activation Parameters in the Competitive Cleavage of C−CN and C−H Bonds in 2-Methyl-3-Butenenitrile Using [(dippe)NiH] 2 journal, July 2008

Deep Hydrodesulfurization in Homogeneous Solution: Access to a Transition-Metal Insertion Complex of 4,6-Dimethyldibenzothiophene journal, July 1998

Evidence for the Existence of a Late-Metal Terminal Sulfido Complex journal, April 1999

Cationic Nickel(II) Complexes of Chelating N-Heterocyclic Carbenes journal, October 1999

Nickel(II) cis - and trans -Dimethyl Complexes of Di-N-heterocyclic Carbenes journal, June 2001

Synthesis, structure and reactivity of NHC–nickel complexes containing carbonato ligands journal, May 2013

Bis-NHC Chelate Complexes of Nickel(0) and Platinum(0) journal, May 2014

Heteroleptic nickel( ii )–diNHC complexes and an unusual ‘reverse’ carbene-transfer reaction to silver( i ) journal, January 2017

Organonickel complexes encumbering bis-imidazolylidene carbene ligands: Synthesis, X-ray structure and catalytic insights on Buchwald-Hartwig amination reactions journal, March 2017

Four-coordinate Co( ii ) and Fe( ii ) complexes with bis(N-heterocyclic carbene)borate and their magnetic properties journal, January 2015

New Structural Motifs of Lithium N-Heterocyclic Carbene Complexes with Bis(3- tert -butylimidazol-2-ylidene)dialkylborate Ligands journal, May 2009

Synthesis and Unexpected Reactivity of Germyliumylidene Hydride [:GeH] + Stabilized by a Bis( N -heterocyclic carbene)borate Ligand journal, July 2014

Metal Nitrosyls. I. Triphenylphosphine Nitrosyl Nickel Complexes journal, January 1964

Four- and Five-Coordinate Nickel(II) Complexes with Trimethylphosphine. journal, January 1969

Synthesis and structural characterization of [BseMe]Ni(PPh3)(NO), a nickel complex with a bent nitrosyl ligand journal, October 2007

General bonding model for linear and bent transition metal-nitrosyl complexes journal, May 1973

Neutral pyrazolyl-bridged nickel nitrosyl complexes. Synthesis, structure, and reactivity journal, December 1979

Insertion of Zerovalent Nickel into the N–N Bond of N-Heterocyclic-Carbene-Activated N 2 O journal, August 2013

Reactivity of a Nickel Sulfide with Carbon Monoxide and Nitric Oxide journal, September 2016

Direct Observation of Noninnocent Reactivity of ZnBr 2 with Alkyl Halide Complexes of Nickel journal, January 2004

Ring Closure of 1,4-Pentadiene to Cyclopentene by a Zwitterionic Nickel Catalyst journal, August 2004

Synthesis, characterization, and norbornene polymerization of η3-benzylnickel(II) complexes of N-heterocyclic carbenes journal, June 2008

Unusual Reactivity of Molecular Oxygen with π-Allylnickel(N-heterocyclic carbene) Chloride Complexes journal, January 2003

Kinetics, Thermodynamics, and Effect of BPh ₃ on Competitive C−C and C−H Bond Activation Reactions in the Interconversion of Allyl Cyanide by [Ni(dippe)]
journal, March 2004

Cleavage of Carbon−Carbon Bonds in Alkyl Cyanides Using Nickel(0)
journal, August 2004

Solvent Effects and Activation Parameters in the Competitive Cleavage of C−CN and C−H Bonds in 2-Methyl-3-Butenenitrile Using [(dippe)NiH] ₂
journal, July 2008

Deep Hydrodesulfurization in Homogeneous Solution: Access to a Transition-Metal Insertion Complex of 4,6-Dimethyldibenzothiophene
journal, July 1998

Evidence for the Existence of a Late-Metal Terminal Sulfido Complex
journal, April 1999

Cationic Nickel(II) Complexes of Chelating N-Heterocyclic Carbenes
journal, October 1999

Nickel(II) cis - and trans -Dimethyl Complexes of Di-N-heterocyclic Carbenes
journal, June 2001

Synthesis, structure and reactivity of NHC–nickel complexes containing carbonato ligands
journal, May 2013

Bis-NHC Chelate Complexes of Nickel(0) and Platinum(0)
journal, May 2014

Heteroleptic nickel( ii )–diNHC complexes and an unusual ‘reverse’ carbene-transfer reaction to silver( i )
journal, January 2017

Organonickel complexes encumbering bis-imidazolylidene carbene ligands: Synthesis, X-ray structure and catalytic insights on Buchwald-Hartwig amination reactions
journal, March 2017

Four-coordinate Co( ii ) and Fe( ii ) complexes with bis(N-heterocyclic carbene)borate and their magnetic properties
journal, January 2015

New Structural Motifs of Lithium N-Heterocyclic Carbene Complexes with Bis(3- tert -butylimidazol-2-ylidene)dialkylborate Ligands
journal, May 2009

Synthesis and Unexpected Reactivity of Germyliumylidene Hydride [:GeH] ⁺ Stabilized by a Bis( N -heterocyclic carbene)borate Ligand
journal, July 2014

Metal Nitrosyls. I. Triphenylphosphine Nitrosyl Nickel Complexes
journal, January 1964

Four- and Five-Coordinate Nickel(II) Complexes with Trimethylphosphine.
journal, January 1969

Synthesis and structural characterization of [BseMe]Ni(PPh3)(NO), a nickel complex with a bent nitrosyl ligand
journal, October 2007

General bonding model for linear and bent transition metal-nitrosyl complexes
journal, May 1973

Neutral pyrazolyl-bridged nickel nitrosyl complexes. Synthesis, structure, and reactivity
journal, December 1979

Insertion of Zerovalent Nickel into the N–N Bond of N-Heterocyclic-Carbene-Activated N ₂ O
journal, August 2013

Reactivity of a Nickel Sulfide with Carbon Monoxide and Nitric Oxide
journal, September 2016

Direct Observation of Noninnocent Reactivity of ZnBr ₂ with Alkyl Halide Complexes of Nickel
journal, January 2004

Ring Closure of 1,4-Pentadiene to Cyclopentene by a Zwitterionic Nickel Catalyst
journal, August 2004

Synthesis, characterization, and norbornene polymerization of η3-benzylnickel(II) complexes of N-heterocyclic carbenes
journal, June 2008

Unusual Reactivity of Molecular Oxygen with π-Allylnickel(N-heterocyclic carbene) Chloride Complexes
journal, January 2003