Tridentate NNN Ligand Associating Amidoquinoline and Iminophosphorane: Synthesis and Coordination to Pd and Ni Centers

Louis Mazaud; Maxime Tricoire; Sophie Bourcier; Marie Cordier; Vincent Gandon; Audrey Auffrant

doi:10.1021/acs.organomet.9b00867

Tridentate NNN Ligand Associating Amidoquinoline and Iminophosphorane: Synthesis and Coordination to Pd and Ni Centers

Louis Mazaud
, Maxime Tricoire
, Sophie Bourcier
, Marie Cordier
, Vincent Gandon
, Audrey Auffrant

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of a tridentate NNN ligand incorporating an amidoquinoline and an iminophosphorane (L^RH; R = Ph, Cy) was carried out. Coordination to Pd^II and Ni^II precursors gave, as expected, square-planar complexes of the general formula [L^RMCl]. The most surprising result came from the reaction of L^PhH with [Ni(COD)₂], which gave a Ni^II phenyl complex bearing a tridentate amidoquinoline-aminophosphine ligand. This rearrangement would result from a proton transfer assisted by the Ni⁰ on stabilization by a phenyl substituent at the phosphorus, as suggested by DFT calculations and complementary experiments. This nickel phenyl complex formed the corresponding benzoyl complex under a CO atmosphere.

Original language	English
Pages (from-to)	719-728
Number of pages	10
Journal	Organometallics
Volume	39
Issue number	5
DOIs	https://doi.org/10.1021/acs.organomet.9b00867
Publication status	Published - 9 Mar 2020
Externally published	Yes

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title = "Tridentate NNN Ligand Associating Amidoquinoline and Iminophosphorane: Synthesis and Coordination to Pd and Ni Centers",

abstract = "The synthesis of a tridentate NNN ligand incorporating an amidoquinoline and an iminophosphorane (LRH; R = Ph, Cy) was carried out. Coordination to PdII and NiII precursors gave, as expected, square-planar complexes of the general formula [LRMCl]. The most surprising result came from the reaction of LPhH with [Ni(COD)2], which gave a NiII phenyl complex bearing a tridentate amidoquinoline-aminophosphine ligand. This rearrangement would result from a proton transfer assisted by the Ni0 on stabilization by a phenyl substituent at the phosphorus, as suggested by DFT calculations and complementary experiments. This nickel phenyl complex formed the corresponding benzoyl complex under a CO atmosphere.",

author = "Louis Mazaud and Maxime Tricoire and Sophie Bourcier and Marie Cordier and Vincent Gandon and Audrey Auffrant",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "9",

doi = "10.1021/acs.organomet.9b00867",

language = "English",

volume = "39",

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journal = "Organometallics",

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TY - JOUR

T1 - Tridentate NNN Ligand Associating Amidoquinoline and Iminophosphorane

T2 - Synthesis and Coordination to Pd and Ni Centers

AU - Mazaud, Louis

AU - Tricoire, Maxime

AU - Bourcier, Sophie

AU - Cordier, Marie

AU - Gandon, Vincent

AU - Auffrant, Audrey

PY - 2020/3/9

Y1 - 2020/3/9

N2 - The synthesis of a tridentate NNN ligand incorporating an amidoquinoline and an iminophosphorane (LRH; R = Ph, Cy) was carried out. Coordination to PdII and NiII precursors gave, as expected, square-planar complexes of the general formula [LRMCl]. The most surprising result came from the reaction of LPhH with [Ni(COD)2], which gave a NiII phenyl complex bearing a tridentate amidoquinoline-aminophosphine ligand. This rearrangement would result from a proton transfer assisted by the Ni0 on stabilization by a phenyl substituent at the phosphorus, as suggested by DFT calculations and complementary experiments. This nickel phenyl complex formed the corresponding benzoyl complex under a CO atmosphere.

AB - The synthesis of a tridentate NNN ligand incorporating an amidoquinoline and an iminophosphorane (LRH; R = Ph, Cy) was carried out. Coordination to PdII and NiII precursors gave, as expected, square-planar complexes of the general formula [LRMCl]. The most surprising result came from the reaction of LPhH with [Ni(COD)2], which gave a NiII phenyl complex bearing a tridentate amidoquinoline-aminophosphine ligand. This rearrangement would result from a proton transfer assisted by the Ni0 on stabilization by a phenyl substituent at the phosphorus, as suggested by DFT calculations and complementary experiments. This nickel phenyl complex formed the corresponding benzoyl complex under a CO atmosphere.

U2 - 10.1021/acs.organomet.9b00867

DO - 10.1021/acs.organomet.9b00867

M3 - Article

AN - SCOPUS:85080090706

SN - 0276-7333

VL - 39

SP - 719

EP - 728

JO - Organometallics

JF - Organometallics

IS - 5

ER -

Tridentate NNN Ligand Associating Amidoquinoline and Iminophosphorane: Synthesis and Coordination to Pd and Ni Centers

Abstract

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