Ni(2,2′:6′,2′′-terpyridine)<sub>2</sub>: a high-spin octahedral formal Ni(0) complex

Cabrera-Lobera, Natalia; del Horno, Estefanía; Quirós, M. Teresa; Buñuel, Elena; Gimeno, Magali; Brennessel, William W.; Neidig, Michael L.; Priego, José Luis; Cárdenas, Diego J.

doi:10.1039/d3dt04247b

Dalton Trans.

2024

DOI: 10.1039/d3dt04247b

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Ni(2,2′:6′,2′′-terpyridine)₂: a high-spin octahedral formal Ni(0) complex

Natalia Cabrera-Lobera,

Estefanía del Horno,

M. Teresa Quirós

et al.

Abstract: We have synthesised and characterised the complex Ni(tpy)2 (tpy = 2,2’:6’,2’’-terpyridine). This formally Ni(0) complex is paramagnetic both in the solid state and in solution (S = 2). The crystal...

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A decarbonylative approach to alkylnickel intermediates and C(sp ³ )-C(sp ³ ) bond formation

Huang,

Akana,

Sanders

et al. 2024

Science

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The myriad nickel-catalyzed cross-coupling reactions rely on the formation of an organonickel intermediate, but limitations in forming monoalkylnickel species have limited options for C(sp 3 ) cross-coupling. The formation of monoalkylnickel(II) species from abundant carboxylic acid esters would be valuable, but carboxylic acid derivatives are primarily decarboxylated to form alkyl radicals that lack the correct reactivity. In this work, we disclose a facile oxidative addition and decarbonylation sequence that forms monoalkylnickel(II) intermediates through a nonradical process. The key ligand, bis(4-methylpyrazole)pyridine, accelerates decarbonylation, stabilizes the alkylnickel(II) intermediate, and destabilizes off-cycle nickel(0) carbonyl species. The utility of this new reactivity in C(sp 3 )-C(sp 3 ) bond formation is demonstrated in a reaction that is challenging by purely radical methods—the selective cross-coupling of primary carboxylic acid esters with primary alkyl iodides.

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A decarbonylative approach to alkylnickel intermediates and C(sp ³ )-C(sp ³ ) bond formation

Huang,

Akana,

Sanders

et al. 2024

Science

View full text Add to dashboard Cite

show abstract

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Ni(2,2′:6′,2′′-terpyridine)₂: a high-spin octahedral formal Ni(0) complex

Abstract: We have synthesised and characterised the complex Ni(tpy)2 (tpy = 2,2’:6’,2’’-terpyridine). This formally Ni(0) complex is paramagnetic both in the solid state and in solution (S = 2). The crystal...

Cited by 1 publication

References 52 publications

A decarbonylative approach to alkylnickel intermediates and C(sp ³ )-C(sp ³ ) bond formation

A decarbonylative approach to alkylnickel intermediates and C(sp ³ )-C(sp ³ ) bond formation

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Ni(2,2′:6′,2′′-terpyridine)2: a high-spin octahedral formal Ni(0) complex

Abstract: We have synthesised and characterised the complex Ni(tpy)2 (tpy = 2,2’:6’,2’’-terpyridine). This formally Ni(0) complex is paramagnetic both in the solid state and in solution (S = 2). The crystal...

Cited by 1 publication

References 52 publications

A decarbonylative approach to alkylnickel intermediates and C(sp 3 )-C(sp 3 ) bond formation

A decarbonylative approach to alkylnickel intermediates and C(sp 3 )-C(sp 3 ) bond formation

Contact Info

Product

Resources

About

Ni(2,2′:6′,2′′-terpyridine)₂: a high-spin octahedral formal Ni(0) complex

A decarbonylative approach to alkylnickel intermediates and C(sp ³ )-C(sp ³ ) bond formation

A decarbonylative approach to alkylnickel intermediates and C(sp ³ )-C(sp ³ ) bond formation