Precursors: Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction

Florian D'Accriscio; Alexia Ohleier; Emmanuel Nicolas; Matthieu Demange; Olivier Thillaye Du Boullay; Nathalie Saffon-Merceron; Marie Fustier-Boutignon; Elixabete Rezabal; Gilles Frison; Noel Nebra; Nicolas Mézailles

doi:10.1021/acs.organomet.9b00834

Precursors: Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction

Florian D'Accriscio
, Alexia Ohleier
, Emmanuel Nicolas
, Matthieu Demange
, Olivier Thillaye Du Boullay
, Nathalie Saffon-Merceron
, Marie Fustier-Boutignon
, Elixabete Rezabal
, Gilles Frison
, Noel Nebra
, Nicolas Mézailles

École Polytechnique

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

Abstract

The complexes (Cy2PC3H6PCy2)Ni(η2-arene) (arene = toluene (3), naphthalene (4)) have been synthesized and studied in detail. Displacement reactions of the toluene ligand afford the complexes (Cy2PC3H6PCy2)Ni(η2-styrene) (5), (Cy2PC3H6PCy2)Ni(PhCN) (6), (Cy2PC3H6PCy2)Ni(CO)2 (7), (Cy2PC3H6PCy2)Ni(PPh3) (8), (Cy2PC3H6PCy2)Ni(PCy3) (9), {(Cy2PC3H6PCy2)Ni}2(μ-H)2 (10), (Cy2PC3H6PCy2)Ni(η2-CO2) (11), and [(Cy2PC3H6PCy2)Ni]2(μ,η2-1,5-COD) (12). The relative rates of ArCl oxidative addition at Ni complexes 3, 4, 6, 8, and 12 have been evaluated experimentally, and the mechanism has been calculated by DFT. Complexes 3 and 4 are efficient catalysts for the Suzuki-Miyaura reaction between chloroarenes and Ar′B(OH)2.

Original language	English
Pages (from-to)	1688-1699
Number of pages	12
Journal	Organometallics
Volume	39
Issue number	10
DOIs	https://doi.org/10.1021/acs.organomet.9b00834
Publication status	Published - 26 May 2020

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title = "Precursors: Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction",

abstract = "The complexes (Cy2PC3H6PCy2)Ni(η2-arene) (arene = toluene (3), naphthalene (4)) have been synthesized and studied in detail. Displacement reactions of the toluene ligand afford the complexes (Cy2PC3H6PCy2)Ni(η2-styrene) (5), (Cy2PC3H6PCy2)Ni(PhCN) (6), (Cy2PC3H6PCy2)Ni(CO)2 (7), (Cy2PC3H6PCy2)Ni(PPh3) (8), (Cy2PC3H6PCy2)Ni(PCy3) (9), \{(Cy2PC3H6PCy2)Ni\}2(μ-H)2 (10), (Cy2PC3H6PCy2)Ni(η2-CO2) (11), and [(Cy2PC3H6PCy2)Ni]2(μ,η2-1,5-COD) (12). The relative rates of ArCl oxidative addition at Ni complexes 3, 4, 6, 8, and 12 have been evaluated experimentally, and the mechanism has been calculated by DFT. Complexes 3 and 4 are efficient catalysts for the Suzuki-Miyaura reaction between chloroarenes and Ar′B(OH)2.",

author = "Florian D'Accriscio and Alexia Ohleier and Emmanuel Nicolas and Matthieu Demange and \{Thillaye Du Boullay\}, Olivier and Nathalie Saffon-Merceron and Marie Fustier-Boutignon and Elixabete Rezabal and Gilles Frison and Noel Nebra and Nicolas M{\'e}zailles",

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

year = "2020",

month = may,

day = "26",

doi = "10.1021/acs.organomet.9b00834",

language = "English",

volume = "39",

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T2 - Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction

AU - D'Accriscio, Florian

AU - Ohleier, Alexia

AU - Nicolas, Emmanuel

AU - Demange, Matthieu

AU - Thillaye Du Boullay, Olivier

AU - Saffon-Merceron, Nathalie

AU - Fustier-Boutignon, Marie

AU - Rezabal, Elixabete

AU - Frison, Gilles

AU - Nebra, Noel

AU - Mézailles, Nicolas

PY - 2020/5/26

Y1 - 2020/5/26

N2 - The complexes (Cy2PC3H6PCy2)Ni(η2-arene) (arene = toluene (3), naphthalene (4)) have been synthesized and studied in detail. Displacement reactions of the toluene ligand afford the complexes (Cy2PC3H6PCy2)Ni(η2-styrene) (5), (Cy2PC3H6PCy2)Ni(PhCN) (6), (Cy2PC3H6PCy2)Ni(CO)2 (7), (Cy2PC3H6PCy2)Ni(PPh3) (8), (Cy2PC3H6PCy2)Ni(PCy3) (9), {(Cy2PC3H6PCy2)Ni}2(μ-H)2 (10), (Cy2PC3H6PCy2)Ni(η2-CO2) (11), and [(Cy2PC3H6PCy2)Ni]2(μ,η2-1,5-COD) (12). The relative rates of ArCl oxidative addition at Ni complexes 3, 4, 6, 8, and 12 have been evaluated experimentally, and the mechanism has been calculated by DFT. Complexes 3 and 4 are efficient catalysts for the Suzuki-Miyaura reaction between chloroarenes and Ar′B(OH)2.

AB - The complexes (Cy2PC3H6PCy2)Ni(η2-arene) (arene = toluene (3), naphthalene (4)) have been synthesized and studied in detail. Displacement reactions of the toluene ligand afford the complexes (Cy2PC3H6PCy2)Ni(η2-styrene) (5), (Cy2PC3H6PCy2)Ni(PhCN) (6), (Cy2PC3H6PCy2)Ni(CO)2 (7), (Cy2PC3H6PCy2)Ni(PPh3) (8), (Cy2PC3H6PCy2)Ni(PCy3) (9), {(Cy2PC3H6PCy2)Ni}2(μ-H)2 (10), (Cy2PC3H6PCy2)Ni(η2-CO2) (11), and [(Cy2PC3H6PCy2)Ni]2(μ,η2-1,5-COD) (12). The relative rates of ArCl oxidative addition at Ni complexes 3, 4, 6, 8, and 12 have been evaluated experimentally, and the mechanism has been calculated by DFT. Complexes 3 and 4 are efficient catalysts for the Suzuki-Miyaura reaction between chloroarenes and Ar′B(OH)2.

UR - https://www.scopus.com/pages/publications/85085640786

U2 - 10.1021/acs.organomet.9b00834

DO - 10.1021/acs.organomet.9b00834

M3 - Article

AN - SCOPUS:85085640786

SN - 0276-7333

VL - 39

SP - 1688

EP - 1699

JO - Organometallics

JF - Organometallics

IS - 10

ER -

Precursors: Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction

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