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

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

doi:10.1002/anie.202200305

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

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

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

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

Keywords

Aryl Bromides
Biaryls
Calcium
Density Functional Theory
Main Group Chemistry

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.202200305Licence: CC BY

Cite this

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title = "Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls",

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

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. 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. Publisher Copyright: {\textcopyright} 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

year = "2022",

month = apr,

day = "25",

doi = "10.1002/anie.202200305",

language = "English",

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T1 - Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls

AU - Hill, Michael

AU - Pearce, Kyle

AU - Dinoi, Chiara

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. 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. Publisher Copyright: © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

PY - 2022/4/25

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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JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

IS - 18

M1 - e202200305

ER -

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

Abstract

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

Keywords

ASJC Scopus subject areas

Access to Document

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Nucleophilic alkaline earth boryls: from conception and theory to application

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