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Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes
[Image: see text] The use of isocyanides as acceptor groups in metal–hydride hydrogen atom transfer (MHAT) coupling reactions with nonactivated alkenes to form heterocycles is described. Monosubstituted alkenes couple and cyclize directly, whereas more substituted alkenes proceed via a two-step, one...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496133/ https://www.ncbi.nlm.nih.gov/pubmed/37644914 http://dx.doi.org/10.1021/acs.orglett.3c02358 |
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author | Puig, Jordi Bonjoch, Josep Bradshaw, Ben |
author_facet | Puig, Jordi Bonjoch, Josep Bradshaw, Ben |
author_sort | Puig, Jordi |
collection | PubMed |
description | [Image: see text] The use of isocyanides as acceptor groups in metal–hydride hydrogen atom transfer (MHAT) coupling reactions with nonactivated alkenes to form heterocycles is described. Monosubstituted alkenes couple and cyclize directly, whereas more substituted alkenes proceed via a two-step, one-pot procedure involving MHAT reductive cyclization followed by a MHAT Minisci coupling upon the addition of acid. To highlight the utility of the methodology, a diverse variety of substituted heterocycles such as phenanthridines, indoles, and isoquinolines were prepared. |
format | Online Article Text |
id | pubmed-10496133 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-104961332023-09-13 Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes Puig, Jordi Bonjoch, Josep Bradshaw, Ben Org Lett [Image: see text] The use of isocyanides as acceptor groups in metal–hydride hydrogen atom transfer (MHAT) coupling reactions with nonactivated alkenes to form heterocycles is described. Monosubstituted alkenes couple and cyclize directly, whereas more substituted alkenes proceed via a two-step, one-pot procedure involving MHAT reductive cyclization followed by a MHAT Minisci coupling upon the addition of acid. To highlight the utility of the methodology, a diverse variety of substituted heterocycles such as phenanthridines, indoles, and isoquinolines were prepared. American Chemical Society 2023-08-30 /pmc/articles/PMC10496133/ /pubmed/37644914 http://dx.doi.org/10.1021/acs.orglett.3c02358 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Puig, Jordi Bonjoch, Josep Bradshaw, Ben Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes |
title | Isocyanides as Acceptor Groups in MHAT Reactions with
Unactivated Alkenes |
title_full | Isocyanides as Acceptor Groups in MHAT Reactions with
Unactivated Alkenes |
title_fullStr | Isocyanides as Acceptor Groups in MHAT Reactions with
Unactivated Alkenes |
title_full_unstemmed | Isocyanides as Acceptor Groups in MHAT Reactions with
Unactivated Alkenes |
title_short | Isocyanides as Acceptor Groups in MHAT Reactions with
Unactivated Alkenes |
title_sort | isocyanides as acceptor groups in mhat reactions with
unactivated alkenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496133/ https://www.ncbi.nlm.nih.gov/pubmed/37644914 http://dx.doi.org/10.1021/acs.orglett.3c02358 |
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