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Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed Arylallylation of Unactivated Alkenes
[Image: see text] Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp(3)-rich scaffolds are of particular importance. Although there are methods for combin...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644603/ https://www.ncbi.nlm.nih.gov/pubmed/31458973 http://dx.doi.org/10.1021/acsomega.8b01021 |
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author | Phillips, David Hewitt, Joanne F. M. France, David J. |
author_facet | Phillips, David Hewitt, Joanne F. M. France, David J. |
author_sort | Phillips, David |
collection | PubMed |
description | [Image: see text] Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp(3)-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp(3)–sp(3) carbon–carbon bonds, these form the carbon–heteroatom bond rather than a carbon–carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon–carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles. |
format | Online Article Text |
id | pubmed-6644603 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66446032019-08-27 Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed Arylallylation of Unactivated Alkenes Phillips, David Hewitt, Joanne F. M. France, David J. ACS Omega [Image: see text] Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently nonplanar shape, new methods of forming sp(3)-rich scaffolds are of particular importance. Although there are methods for combining heterocyclization and formation of new sp(3)–sp(3) carbon–carbon bonds, these form the carbon–heteroatom bond rather than a carbon–carbon bond of the heterocycle. Here, we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon–carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3-disubstituted heterocycles. American Chemical Society 2018-07-31 /pmc/articles/PMC6644603/ /pubmed/31458973 http://dx.doi.org/10.1021/acsomega.8b01021 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Phillips, David Hewitt, Joanne F. M. France, David J. Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed Arylallylation of Unactivated Alkenes |
title | Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed
Arylallylation of Unactivated Alkenes |
title_full | Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed
Arylallylation of Unactivated Alkenes |
title_fullStr | Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed
Arylallylation of Unactivated Alkenes |
title_full_unstemmed | Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed
Arylallylation of Unactivated Alkenes |
title_short | Synthesis of 3,3-Disubstituted Heterocycles by Pd-Catalyzed
Arylallylation of Unactivated Alkenes |
title_sort | synthesis of 3,3-disubstituted heterocycles by pd-catalyzed
arylallylation of unactivated alkenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644603/ https://www.ncbi.nlm.nih.gov/pubmed/31458973 http://dx.doi.org/10.1021/acsomega.8b01021 |
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