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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...

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Autores principales: Phillips, David, Hewitt, Joanne F. M., France, David J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
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.
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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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