Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study

Duo Wei; Omar Sadek; Vincent Dorcet; Thierry Roisnel; Christophe Darcel; Emmanuel Gras; Eric Clot; Jean Baptiste Sortais

doi:10.1016/j.jcat.2018.08.008

Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study

Duo Wei
, Omar Sadek
, Vincent Dorcet
, Thierry Roisnel
, Christophe Darcel
, Emmanuel Gras
, Eric Clot
, Jean Baptiste Sortais^*

^*Corresponding author for this work

Université de Rennes
Toulouse University, UPS-OMP, IRAP
Université Montpellier
Institut universitaire de France

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

79 Scopus citations

Abstract

The selective mono-N-methylation of anilines using methanol as an alkylating reagent was achieved with high efficiency under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands and in the presence of a base. The reaction proceeds well for a large scope of anilines (32 examples) with low loadings of both the catalyst (down to 0.5 mol%) and the base (Cs₂CO₃, down to 5 mol%). The mechanism of the reaction was investigated by DFT (PBE0-D3) calculations.

Original language	English
Pages (from-to)	300-309
Number of pages	10
Journal	Journal of Catalysis
Volume	366
DOIs	https://doi.org/10.1016/j.jcat.2018.08.008
State	Published - Oct 2018
Externally published	Yes

Keywords

Amines
DFT-D3 calculations
Hydrogen borrowing
Mechanism
Methanol
Methylation
Rhenium

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10.1016/j.jcat.2018.08.008

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title = "Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study",

abstract = "The selective mono-N-methylation of anilines using methanol as an alkylating reagent was achieved with high efficiency under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands and in the presence of a base. The reaction proceeds well for a large scope of anilines (32 examples) with low loadings of both the catalyst (down to 0.5 mol\%) and the base (Cs2CO3, down to 5 mol\%). The mechanism of the reaction was investigated by DFT (PBE0-D3) calculations.",

keywords = "Amines, DFT-D3 calculations, Hydrogen borrowing, Mechanism, Methanol, Methylation, Rhenium",

author = "Duo Wei and Omar Sadek and Vincent Dorcet and Thierry Roisnel and Christophe Darcel and Emmanuel Gras and Eric Clot and Sortais, \{Jean Baptiste\}",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Inc.",

year = "2018",

month = oct,

doi = "10.1016/j.jcat.2018.08.008",

language = "英语",

volume = "366",

pages = "300--309",

journal = "Journal of Catalysis",

issn = "0021-9517",

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T1 - Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes

T2 - An experimental and theoretical study

AU - Wei, Duo

AU - Sadek, Omar

AU - Dorcet, Vincent

AU - Roisnel, Thierry

AU - Darcel, Christophe

AU - Gras, Emmanuel

AU - Clot, Eric

AU - Sortais, Jean Baptiste

PY - 2018/10

Y1 - 2018/10

N2 - The selective mono-N-methylation of anilines using methanol as an alkylating reagent was achieved with high efficiency under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands and in the presence of a base. The reaction proceeds well for a large scope of anilines (32 examples) with low loadings of both the catalyst (down to 0.5 mol%) and the base (Cs2CO3, down to 5 mol%). The mechanism of the reaction was investigated by DFT (PBE0-D3) calculations.

AB - The selective mono-N-methylation of anilines using methanol as an alkylating reagent was achieved with high efficiency under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands and in the presence of a base. The reaction proceeds well for a large scope of anilines (32 examples) with low loadings of both the catalyst (down to 0.5 mol%) and the base (Cs2CO3, down to 5 mol%). The mechanism of the reaction was investigated by DFT (PBE0-D3) calculations.

KW - Amines

KW - DFT-D3 calculations

KW - Hydrogen borrowing

KW - Mechanism

KW - Methanol

KW - Methylation

KW - Rhenium

UR - https://www.scopus.com/pages/publications/85052934589

U2 - 10.1016/j.jcat.2018.08.008

DO - 10.1016/j.jcat.2018.08.008

M3 - 文章

AN - SCOPUS:85052934589

SN - 0021-9517

VL - 366

SP - 300

EP - 309

JO - Journal of Catalysis

JF - Journal of Catalysis

ER -

Selective mono N-methylation of anilines with methanol catalyzed by rhenium complexes: An experimental and theoretical study

Abstract

Keywords

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