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Selective Synthesis of (Benzyl)biphenyls by Successive Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl Acetate under Air Atmosphere

[Image: see text] An efficient Pd-catalyzed cross-coupling reaction of phenylboronic acids and benzyl carbonates was developed, producing diarylmethanes. Benzyl acetates could also be used as coupling partners instead of benzyl carbonates, affording diarylmethanes in comparable yields. This reaction...

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Detalles Bibliográficos
Autores principales: Ohsumi, Masato, Nishiwaki, Nagatoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645156/
https://www.ncbi.nlm.nih.gov/pubmed/31457333
http://dx.doi.org/10.1021/acsomega.7b01450
Descripción
Sumario:[Image: see text] An efficient Pd-catalyzed cross-coupling reaction of phenylboronic acids and benzyl carbonates was developed, producing diarylmethanes. Benzyl acetates could also be used as coupling partners instead of benzyl carbonates, affording diarylmethanes in comparable yields. This reaction can be conducted under air atmosphere without any care for moisture and oxygen. The ester function showed an intermediate reactivity between chloro and bromo groups. This property facilitated the selective synthesis of diverse (benzyl)biphenyls by successive Suzuki–Miyaura coupling reactions using bromo- and chloro-substituted benzyl esters with two types of boronic acids.