Synthesis of Molecular Phenylcalcium Derivatives: Application to the Formation of Biaryls. Issue 18 (7th March 2022)

• Record Type: Journal Article
• Authors: Pearce, Kyle G.; Dinoi, Chiara; Hill, Michael S.; Mahon, Mary F.; Maron, Laurent; Schwamm, Ryan S.; Wilson, Andrew S. S.
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 18(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-07
• Subjects: Aryl Bromides -- Biaryls -- Calcium -- Density Functional Theory -- Main Group Chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202200305
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Hydrocarbon‐soluble β‐diketiminato phenylcalcium derivatives, which display various modes of Ca−μ2 ‐Ph−Ca bridging, are accessible from reactions of Ph2 Hg 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. Abstract : Isolable and hydrocarbon‐soluble β‐diketiminato calcium phenyls are accessible from the reaction of Ph2 Hg and [(BDI)CaH]2 . The compounds were shown to react with bromoarenes through a direct SN Ar displacement of halide, leading to the uncatalyzed formation of biaryl molecules.