Alkane carbon-hydrogen bond functionalization with (NHC)MCl precatalysts (M = Cu, Au ; NHC=N-heterocyclic carbene)

MR Fructos; P de Fremont; Steven Patrick Nolan; MM Diaz-Requejo; PJ Perez

doi:10.1021/om0507474

Alkane carbon-hydrogen bond functionalization with (NHC)MCl precatalysts (M = Cu, Au ; NHC=N-heterocyclic carbene)

MR Fructos, P de Fremont, Steven Patrick Nolan, MM Diaz-Requejo, PJ Perez

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Abstract

Facile alkane functionalization by means of the insertion of :CHCO2Et, from ethyl diazoacetate, into carbon-hydrogen bonds mediated by catalytic amounts of (NHC)MCI (NHC = N-heterocyclic ligand; M = Cu, Au) and a halide scavenger MX has been achieved. This chemistry includes the insertion of the carbene fragment into alkane primary positions with Cu- and Au-based catalysts. The nature of the counterion X and of the NHC ligand have a significant effect on the overall yields and regioselectivity of the reaction.

Original language	English
Pages (from-to)	2237-2241
Number of pages	5
Journal	Organometallics
Volume	25
Issue number	9
DOIs	https://doi.org/10.1021/om0507474
Publication status	Published - 24 Apr 2006

Keywords

METAL-CATALYZED REACTIONS
ETHYL DIAZOACETATE
H ACTIVATION
ENHANCED ATTACK
INSERTION
DIAZOESTERS
COMPLEXES
CYCLOPROPANATION
CARBOXYLATES
HOMOLOGATION

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title = "Alkane carbon-hydrogen bond functionalization with (NHC)MCl precatalysts (M = Cu, Au ; NHC=N-heterocyclic carbene)",

abstract = "Facile alkane functionalization by means of the insertion of :CHCO2Et, from ethyl diazoacetate, into carbon-hydrogen bonds mediated by catalytic amounts of (NHC)MCI (NHC = N-heterocyclic ligand; M = Cu, Au) and a halide scavenger MX has been achieved. This chemistry includes the insertion of the carbene fragment into alkane primary positions with Cu- and Au-based catalysts. The nature of the counterion X and of the NHC ligand have a significant effect on the overall yields and regioselectivity of the reaction.",

keywords = "METAL-CATALYZED REACTIONS, ETHYL DIAZOACETATE, H ACTIVATION, ENHANCED ATTACK, INSERTION, DIAZOESTERS, COMPLEXES, CYCLOPROPANATION, CARBOXYLATES, HOMOLOGATION",

author = "MR Fructos and \{de Fremont\}, P and Nolan, \{Steven Patrick\} and MM Diaz-Requejo and PJ Perez",

year = "2006",

month = apr,

day = "24",

doi = "10.1021/om0507474",

language = "English",

volume = "25",

pages = "2237--2241",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "9",

}

TY - JOUR

T1 - Alkane carbon-hydrogen bond functionalization with (NHC)MCl precatalysts (M = Cu, Au ; NHC=N-heterocyclic carbene)

AU - Fructos, MR

AU - de Fremont, P

AU - Nolan, Steven Patrick

AU - Diaz-Requejo, MM

AU - Perez, PJ

PY - 2006/4/24

Y1 - 2006/4/24

N2 - Facile alkane functionalization by means of the insertion of :CHCO2Et, from ethyl diazoacetate, into carbon-hydrogen bonds mediated by catalytic amounts of (NHC)MCI (NHC = N-heterocyclic ligand; M = Cu, Au) and a halide scavenger MX has been achieved. This chemistry includes the insertion of the carbene fragment into alkane primary positions with Cu- and Au-based catalysts. The nature of the counterion X and of the NHC ligand have a significant effect on the overall yields and regioselectivity of the reaction.

AB - Facile alkane functionalization by means of the insertion of :CHCO2Et, from ethyl diazoacetate, into carbon-hydrogen bonds mediated by catalytic amounts of (NHC)MCI (NHC = N-heterocyclic ligand; M = Cu, Au) and a halide scavenger MX has been achieved. This chemistry includes the insertion of the carbene fragment into alkane primary positions with Cu- and Au-based catalysts. The nature of the counterion X and of the NHC ligand have a significant effect on the overall yields and regioselectivity of the reaction.

KW - METAL-CATALYZED REACTIONS

KW - ETHYL DIAZOACETATE

KW - H ACTIVATION

KW - ENHANCED ATTACK

KW - INSERTION

KW - DIAZOESTERS

KW - COMPLEXES

KW - CYCLOPROPANATION

KW - CARBOXYLATES

KW - HOMOLOGATION

UR - https://www.scopus.com/pages/publications/33646420086

U2 - 10.1021/om0507474

DO - 10.1021/om0507474

M3 - Article

SN - 0276-7333

VL - 25

SP - 2237

EP - 2241

JO - Organometallics

JF - Organometallics

IS - 9

ER -

Alkane carbon-hydrogen bond functionalization with (NHC)MCl precatalysts (M = Cu, Au ; NHC=N-heterocyclic carbene)

Abstract

Keywords

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