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

Hydrocarbon‐soluble β‐diketiminato phenylcalcium derivatives, which display various modes of Ca−μ2‐Ph−Ca bridging, are accessible from reactions of Ph2Hg and [(BDI)CaH]2. Although the resultant compounds are inert toward the C−H bonds of benzene, they yield selective and uncatalyzed biaryl formation...

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Published inAngewandte Chemie International Edition Vol. 61; no. 18; pp. e202200305 - n/a
Main Authors Pearce, Kyle G., Dinoi, Chiara, Hill, Michael S., Mahon, Mary F., Maron, Laurent, Schwamm, Ryan S., Wilson, Andrew S. S.
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 25.04.2022
Wiley-VCH Verlag
John Wiley and Sons Inc
EditionInternational ed. in English
Subjects
Aryl Bromides
Benzene
Biaryls
Bromides
Calcium
Chemical bonds
Chemical Physics
Chemical synthesis
Communication
Communications
Density Functional Theory
Main Group Chemistry
Physics
Main Group Chemistry
Aryl Bromides
Calcium
Biaryls
Density Functional Theory
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Summary:Hydrocarbon‐soluble β‐diketiminato phenylcalcium derivatives, which display various modes of Ca−μ2‐Ph−Ca bridging, are accessible from reactions of Ph2Hg 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. Isolable and hydrocarbon‐soluble β‐diketiminato calcium phenyls are accessible from the reaction of Ph2Hg and [(BDI)CaH]2. The compounds were shown to react with bromoarenes through a direct SNAr displacement of halide, leading to the uncatalyzed formation of biaryl molecules.
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PMCID: PMC9315018
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202200305