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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2017
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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 |
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author | Ohsumi, Masato Nishiwaki, Nagatoshi |
author_facet | Ohsumi, Masato Nishiwaki, Nagatoshi |
author_sort | Ohsumi, Masato |
collection | PubMed |
description | [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. |
format | Online Article Text |
id | pubmed-6645156 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66451562019-08-27 Selective Synthesis of (Benzyl)biphenyls by Successive Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl Acetate under Air Atmosphere Ohsumi, Masato Nishiwaki, Nagatoshi ACS Omega [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. American Chemical Society 2017-11-09 /pmc/articles/PMC6645156/ /pubmed/31457333 http://dx.doi.org/10.1021/acsomega.7b01450 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Ohsumi, Masato Nishiwaki, Nagatoshi Selective Synthesis of (Benzyl)biphenyls by Successive Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl Acetate under Air Atmosphere |
title | Selective Synthesis of (Benzyl)biphenyls by Successive
Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl
Acetate under Air Atmosphere |
title_full | Selective Synthesis of (Benzyl)biphenyls by Successive
Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl
Acetate under Air Atmosphere |
title_fullStr | Selective Synthesis of (Benzyl)biphenyls by Successive
Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl
Acetate under Air Atmosphere |
title_full_unstemmed | Selective Synthesis of (Benzyl)biphenyls by Successive
Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl
Acetate under Air Atmosphere |
title_short | Selective Synthesis of (Benzyl)biphenyls by Successive
Suzuki–Miyaura Coupling of Phenylboronic Acids with 4-Bromobenzyl
Acetate under Air Atmosphere |
title_sort | selective synthesis of (benzyl)biphenyls by successive
suzuki–miyaura coupling of phenylboronic acids with 4-bromobenzyl
acetate under air atmosphere |
url | 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 |
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