Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls

Kyle Pearce; Chiara Dinoi; Michael Hill; Mary Mahon; Laurent Maron; Ryan Schwamm; Andrew Wilson

doi:10.1002/anie.202200305

Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls

Kyle Pearce, Chiara Dinoi, Michael Hill, Mary Mahon, Laurent Maron, Ryan Schwamm, Andrew Wilson

Université de Toulouse

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

9 Citations (SciVal)

Abstract

Hydrocarbon-soluble β-diketiminato phenylcalcium derivatives, which display various modes of Ca−μ ₂-Ph−Ca bridging, are accessible from reactions of Ph ₂Hg and [(BDI)CaH] ₂. Although the resultant compounds are inert toward the C−H bonds of benzene, they yield selective and uncatalyzed biaryl formation when reacted with readily available aryl bromides.

Original language	English
Article number	e202200305
Journal	Angewandte Chemie International Edition
Volume	61
Issue number	18
Early online date	7 Mar 2022
DOIs	https://doi.org/10.1002/anie.202200305
Publication status	Published - 25 Apr 2022

Bibliographical note

Funding Information:
We thank the EPSRC (EP/R020752/1) for support of this research and the Royal Commission for the Exhibition of 1851 for the provision of a Postdoctoral Fellowship (R.J.S.). L.M. is a senior member of the Institut Universitaire de France. CalMip is acknowledged for a generous grant of computing time.

Keywords

Aryl Bromides
Biaryls
Calcium
Density Functional Theory
Main Group Chemistry

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.202200305Licence: CC BY

Cite this

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abstract = "Hydrocarbon-soluble β-diketiminato phenylcalcium derivatives, which display various modes of Ca−μ 2-Ph−Ca bridging, are accessible from reactions of Ph 2Hg and [(BDI)CaH] 2. Although the resultant compounds are inert toward the C−H bonds of benzene, they yield selective and uncatalyzed biaryl formation when reacted with readily available aryl bromides. ",

keywords = "Aryl Bromides, Biaryls, Calcium, Density Functional Theory, Main Group Chemistry",

author = "Kyle Pearce and Chiara Dinoi and Michael Hill and Mary Mahon and Laurent Maron and Ryan Schwamm and Andrew Wilson",

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AU - Pearce, Kyle

AU - Dinoi, Chiara

AU - Hill, Michael

AU - Mahon, Mary

AU - Maron, Laurent

AU - Schwamm, Ryan

AU - Wilson, Andrew

N1 - Funding Information: We thank the EPSRC (EP/R020752/1) for support of this research and the Royal Commission for the Exhibition of 1851 for the provision of a Postdoctoral Fellowship (R.J.S.). L.M. is a senior member of the Institut Universitaire de France. CalMip is acknowledged for a generous grant of computing time.

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Y1 - 2022/4/25

N2 - Hydrocarbon-soluble β-diketiminato phenylcalcium derivatives, which display various modes of Ca−μ 2-Ph−Ca bridging, are accessible from reactions of Ph 2Hg and [(BDI)CaH] 2. Although the resultant compounds are inert toward the C−H bonds of benzene, they yield selective and uncatalyzed biaryl formation when reacted with readily available aryl bromides.

AB - Hydrocarbon-soluble β-diketiminato phenylcalcium derivatives, which display various modes of Ca−μ 2-Ph−Ca bridging, are accessible from reactions of Ph 2Hg and [(BDI)CaH] 2. Although the resultant compounds are inert toward the C−H bonds of benzene, they yield selective and uncatalyzed biaryl formation when reacted with readily available aryl bromides.

KW - Aryl Bromides

KW - Biaryls

KW - Calcium

KW - Density Functional Theory

KW - Main Group Chemistry

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Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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Nucleophilic alkaline earth boryls: from conception and theory to application

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Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

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Nucleophilic alkaline earth boryls: from conception and theory to application

Cite this