Room-temperature palladium-catalyzed Negishi-type coupling: A combined experimental and theoretical study

Philippe Ribagnac; Matthias Blug; Jose Villa-Uribe; Xavier Frédéric Le Goff; Corinne Gosmini; Nicolas Mézailles

doi:10.1002/chem.201102369

Room-temperature palladium-catalyzed Negishi-type coupling: A combined experimental and theoretical study

Philippe Ribagnac, Matthias Blug, Jose Villa-Uribe, Xavier Frédéric Le Goff, Corinne Gosmini, Nicolas Mézailles

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

Abstract

An air-stable, bulky electron-accepting phosphine ligand (phosphabarrelene) allows the easy reduction of a Pd ^II precursor to a Pd ⁰ complex, highly active in room-temperature Negishi-type cross-coupling. DFT calculations show that the use of the electron-accepting ligand favors both transmetalation (TM) and reductive-elimination (RE) processes (see scheme; OA=oxidative addition).

Original language	English
Pages (from-to)	14389-14393
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	51
DOIs	https://doi.org/10.1002/chem.201102369
Publication status	Published - 16 Dec 2011
Externally published	Yes

Keywords

Negishi reaction
computational chemistry
cross-coupling
phosphabarrelene ligands
phosphines

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10.1002/chem.201102369

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abstract = "An air-stable, bulky electron-accepting phosphine ligand (phosphabarrelene) allows the easy reduction of a Pd II precursor to a Pd 0 complex, highly active in room-temperature Negishi-type cross-coupling. DFT calculations show that the use of the electron-accepting ligand favors both transmetalation (TM) and reductive-elimination (RE) processes (see scheme; OA=oxidative addition).",

keywords = "Negishi reaction, computational chemistry, cross-coupling, phosphabarrelene ligands, phosphines",

author = "Philippe Ribagnac and Matthias Blug and Jose Villa-Uribe and \{Le Goff\}, \{Xavier Fr{\'e}d{\'e}ric\} and Corinne Gosmini and Nicolas M{\'e}zailles",

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doi = "10.1002/chem.201102369",

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journal = "Chemistry - A European Journal",

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T2 - A combined experimental and theoretical study

AU - Ribagnac, Philippe

AU - Blug, Matthias

AU - Villa-Uribe, Jose

AU - Le Goff, Xavier Frédéric

AU - Gosmini, Corinne

AU - Mézailles, Nicolas

PY - 2011/12/16

Y1 - 2011/12/16

N2 - An air-stable, bulky electron-accepting phosphine ligand (phosphabarrelene) allows the easy reduction of a Pd II precursor to a Pd 0 complex, highly active in room-temperature Negishi-type cross-coupling. DFT calculations show that the use of the electron-accepting ligand favors both transmetalation (TM) and reductive-elimination (RE) processes (see scheme; OA=oxidative addition).

AB - An air-stable, bulky electron-accepting phosphine ligand (phosphabarrelene) allows the easy reduction of a Pd II precursor to a Pd 0 complex, highly active in room-temperature Negishi-type cross-coupling. DFT calculations show that the use of the electron-accepting ligand favors both transmetalation (TM) and reductive-elimination (RE) processes (see scheme; OA=oxidative addition).

KW - Negishi reaction

KW - computational chemistry

KW - cross-coupling

KW - phosphabarrelene ligands

KW - phosphines

U2 - 10.1002/chem.201102369

DO - 10.1002/chem.201102369

M3 - Article

AN - SCOPUS:83755178370

SN - 0947-6539

VL - 17

SP - 14389

EP - 14393

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 51

ER -

Room-temperature palladium-catalyzed Negishi-type coupling: A combined experimental and theoretical study

Abstract

Keywords

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