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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...

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Autores principales: Puig, Jordi, Bonjoch, Josep, Bradshaw, Ben
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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