Regiospecific C-H bond activation: Reversible H/D exchange promoted by CuI complexes with triazamacrocyclic ligands

Xavi Ribas; Raül Xifra; Teodor Parella; Albert Poater; Miquel Solà; Antoni Llobet

doi:10.1002/anie.200504222

Regiospecific C-H bond activation: Reversible H/D exchange promoted by Cu^I complexes with triazamacrocyclic ligands

Xavi Ribas, Raül Xifra, Teodor Parella, Albert Poater, Miquel Solà, Antoni Llobet

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

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) The first reversible and regiospecific H/D exchange promoted by CuI proceeds in weakly coordinating deuterated "acidic" solvents, such as [D6]acetone or [D 4]methanol (see scheme). The kinetics of the reaction have been studied in both directions (H/D and D/H exchange) by 1H and 2H NMR spectroscopy, and a molecular mechanism is proposed that is in accordance with all experimental and theoretical data. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

Original language	English
Pages (from-to)	2941-2944
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	18
DOIs	https://doi.org/10.1002/anie.200504222
Publication status	Published - 28 Apr 2006

Keywords

Agostic interactions
C-H activation
Copper
Density functional calculations
Isotopic labeling

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10.1002/anie.200504222

Cite this

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title = "Regiospecific C-H bond activation: Reversible H/D exchange promoted by CuI complexes with triazamacrocyclic ligands",

abstract = "(Chemical Equation Presented) The first reversible and regiospecific H/D exchange promoted by CuI proceeds in weakly coordinating deuterated {"}acidic{"} solvents, such as [D6]acetone or [D 4]methanol (see scheme). The kinetics of the reaction have been studied in both directions (H/D and D/H exchange) by 1H and 2H NMR spectroscopy, and a molecular mechanism is proposed that is in accordance with all experimental and theoretical data. {\textcopyright} 2006 Wiley-VCH Verlag GmbH \& Co. KGaA.",

keywords = "Agostic interactions, C-H activation, Copper, Density functional calculations, Isotopic labeling",

author = "Xavi Ribas and Ra{\"u}l Xifra and Teodor Parella and Albert Poater and Miquel Sol{\`a} and Antoni Llobet",

note = "This research was supported by the MEC (Spain; projects BQU2003-02884, BQU2003-01677, and CTQ2005-08797-C02-01). X.R. is grateful for a Juan de la Cierva contract from MEC",

year = "2006",

month = apr,

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doi = "10.1002/anie.200504222",

language = "English",

volume = "45",

pages = "2941--2944",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Regiospecific C-H bond activation: Reversible H/D exchange promoted by CuI complexes with triazamacrocyclic ligands

AU - Ribas, Xavi

AU - Xifra, Raül

AU - Parella, Teodor

AU - Poater, Albert

AU - Solà, Miquel

AU - Llobet, Antoni

N1 - This research was supported by the MEC (Spain; projects BQU2003-02884, BQU2003-01677, and CTQ2005-08797-C02-01). X.R. is grateful for a Juan de la Cierva contract from MEC

PY - 2006/4/28

Y1 - 2006/4/28

N2 - (Chemical Equation Presented) The first reversible and regiospecific H/D exchange promoted by CuI proceeds in weakly coordinating deuterated "acidic" solvents, such as [D6]acetone or [D 4]methanol (see scheme). The kinetics of the reaction have been studied in both directions (H/D and D/H exchange) by 1H and 2H NMR spectroscopy, and a molecular mechanism is proposed that is in accordance with all experimental and theoretical data. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

AB - (Chemical Equation Presented) The first reversible and regiospecific H/D exchange promoted by CuI proceeds in weakly coordinating deuterated "acidic" solvents, such as [D6]acetone or [D 4]methanol (see scheme). The kinetics of the reaction have been studied in both directions (H/D and D/H exchange) by 1H and 2H NMR spectroscopy, and a molecular mechanism is proposed that is in accordance with all experimental and theoretical data. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

KW - Agostic interactions

KW - C-H activation

KW - Copper

KW - Density functional calculations

KW - Isotopic labeling

UR - https://www.scopus.com/pages/publications/33746191861

U2 - 10.1002/anie.200504222

DO - 10.1002/anie.200504222

M3 - Article

SN - 1433-7851

VL - 45

SP - 2941

EP - 2944

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 18

ER -

Regiospecific C-H bond activation: Reversible H/D exchange promoted by Cu^I complexes with triazamacrocyclic ligands

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Modelización molecular de procesos bioinorgánicos de interés tecnológico (MOMOBIT)

Constants d'acoplament escalars, dipolars i coeficients de difusió per RMN. Nous mètodes i aplicació a molècules en abundància natural i biomolècules marcades isotòpicament

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Regiospecific C-H bond activation: Reversible H/D exchange promoted by CuI complexes with triazamacrocyclic ligands

Abstract

Keywords

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Other files and links

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Projects

Modelización molecular de procesos bioinorgánicos de interés tecnológico (MOMOBIT)

Constants d'acoplament escalars, dipolars i coeficients de difusió per RMN. Nous mètodes i aplicació a molècules en abundància natural i biomolècules marcades isotòpicament

Cite this

Regiospecific C-H bond activation: Reversible H/D exchange promoted by Cu^I complexes with triazamacrocyclic ligands