[Pd(IPr*)(3-Cl-pyridinyl)Cl-2]: A Novel and Efficient PEPPSI Precatalyst

Anthony Chartoire; Xavier Frogneux; Arnaud Boreux; Alexandra M. Z. Slawin; Steven P. Nolan

doi:10.1021/om300725f

[Pd(IPr*)(3-Cl-pyridinyl)Cl-2]: A Novel and Efficient PEPPSI Precatalyst

Anthony Chartoire, Xavier Frogneux, Arnaud Boreux, Alexandra M. Z. Slawin, Steven P. Nolan

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

Abstract

The preparation of the novel, well-defined [Pd(IPr*)(3-Cl-pyridinyl)Cl-2] complex is described. The steric parameters of the ligand as well as its reactivity in the Buchwald-Hartwig amination were directly compared to other [Pd(NHC)(3-Cl-pyridinyl)Cl-2] and [Pd(IPr*)(LX)Cl)] precatalysts (LX = cinnamyl or acac). The title complex exhibits similar catalytic activity to [Pd(NHC)(3-Cl-pyridinyl)Cl-2] congeners (NHC = IPr and SIPr) at room temperature. However, it also showed improved reactivity at low catalyst loading and high temperature (as low as 0.025 mol %). On the other hand, it proved to be as efficient as the previously reported [Pd(IPr*)(cinnamyl)Cl] complex, pointing to the most likely existence of a similar catalytically active species.

Original language	English
Pages (from-to)	6947-6951
Number of pages	5
Journal	Organometallics
Volume	31
Issue number	19
DOIs	https://doi.org/10.1021/om300725f
Publication status	Published - 8 Oct 2012

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@article{9060aa700ded4b97b391102d397da673,

title = "[Pd(IPr*)(3-Cl-pyridinyl)Cl-2]: A Novel and Efficient PEPPSI Precatalyst",

abstract = "The preparation of the novel, well-defined [Pd(IPr*)(3-Cl-pyridinyl)Cl-2] complex is described. The steric parameters of the ligand as well as its reactivity in the Buchwald-Hartwig amination were directly compared to other [Pd(NHC)(3-Cl-pyridinyl)Cl-2] and [Pd(IPr*)(LX)Cl)] precatalysts (LX = cinnamyl or acac). The title complex exhibits similar catalytic activity to [Pd(NHC)(3-Cl-pyridinyl)Cl-2] congeners (NHC = IPr and SIPr) at room temperature. However, it also showed improved reactivity at low catalyst loading and high temperature (as low as 0.025 mol %). On the other hand, it proved to be as efficient as the previously reported [Pd(IPr*)(cinnamyl)Cl] complex, pointing to the most likely existence of a similar catalytically active species.",

author = "Anthony Chartoire and Xavier Frogneux and Arnaud Boreux and Slawin, {Alexandra M. Z.} and Nolan, {Steven P.}",

year = "2012",

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doi = "10.1021/om300725f",

language = "English",

volume = "31",

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journal = "Organometallics",

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publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - [Pd(IPr*)(3-Cl-pyridinyl)Cl-2]: A Novel and Efficient PEPPSI Precatalyst

AU - Chartoire, Anthony

AU - Frogneux, Xavier

AU - Boreux, Arnaud

AU - Slawin, Alexandra M. Z.

AU - Nolan, Steven P.

PY - 2012/10/8

Y1 - 2012/10/8

N2 - The preparation of the novel, well-defined [Pd(IPr*)(3-Cl-pyridinyl)Cl-2] complex is described. The steric parameters of the ligand as well as its reactivity in the Buchwald-Hartwig amination were directly compared to other [Pd(NHC)(3-Cl-pyridinyl)Cl-2] and [Pd(IPr*)(LX)Cl)] precatalysts (LX = cinnamyl or acac). The title complex exhibits similar catalytic activity to [Pd(NHC)(3-Cl-pyridinyl)Cl-2] congeners (NHC = IPr and SIPr) at room temperature. However, it also showed improved reactivity at low catalyst loading and high temperature (as low as 0.025 mol %). On the other hand, it proved to be as efficient as the previously reported [Pd(IPr*)(cinnamyl)Cl] complex, pointing to the most likely existence of a similar catalytically active species.

AB - The preparation of the novel, well-defined [Pd(IPr*)(3-Cl-pyridinyl)Cl-2] complex is described. The steric parameters of the ligand as well as its reactivity in the Buchwald-Hartwig amination were directly compared to other [Pd(NHC)(3-Cl-pyridinyl)Cl-2] and [Pd(IPr*)(LX)Cl)] precatalysts (LX = cinnamyl or acac). The title complex exhibits similar catalytic activity to [Pd(NHC)(3-Cl-pyridinyl)Cl-2] congeners (NHC = IPr and SIPr) at room temperature. However, it also showed improved reactivity at low catalyst loading and high temperature (as low as 0.025 mol %). On the other hand, it proved to be as efficient as the previously reported [Pd(IPr*)(cinnamyl)Cl] complex, pointing to the most likely existence of a similar catalytically active species.

U2 - 10.1021/om300725f

DO - 10.1021/om300725f

M3 - Article

SN - 0276-7333

VL - 31

SP - 6947

EP - 6951

JO - Organometallics

JF - Organometallics

IS - 19

ER -

[Pd(IPr*)(3-Cl-pyridinyl)Cl-2]: A Novel and Efficient PEPPSI Precatalyst

Abstract

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