Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms

[Image: see text] A highly facile, straightforward synthesis of 1-(3-indolyl)-tetrahydroisoquinolines was developed using either simple copper or iron catalysts. N-protected and unprotected tetrahydroisoquinolines (THIQ) could be used as starting materials. Extension of the substrate scope of the pr...

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Autores principales: Ghobrial, Michael, Schnürch, Michael, Mihovilovic, Marko D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2011
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3226323/
https://www.ncbi.nlm.nih.gov/pubmed/21902275
http://dx.doi.org/10.1021/jo201511d
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author Ghobrial, Michael
Schnürch, Michael
Mihovilovic, Marko D.
author_facet Ghobrial, Michael
Schnürch, Michael
Mihovilovic, Marko D.
author_sort Ghobrial, Michael
collection PubMed
description [Image: see text] A highly facile, straightforward synthesis of 1-(3-indolyl)-tetrahydroisoquinolines was developed using either simple copper or iron catalysts. N-protected and unprotected tetrahydroisoquinolines (THIQ) could be used as starting materials. Extension of the substrate scope of the pronucleophile from indoles to pyrroles and electron-rich arenes was realized. Additionally, methoxyphenylation is not limited to THIQ but can be carried out on isochroman as well, again employing iron and copper catalysis.
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spelling pubmed-32263232011-11-29 Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms Ghobrial, Michael Schnürch, Michael Mihovilovic, Marko D. J Org Chem [Image: see text] A highly facile, straightforward synthesis of 1-(3-indolyl)-tetrahydroisoquinolines was developed using either simple copper or iron catalysts. N-protected and unprotected tetrahydroisoquinolines (THIQ) could be used as starting materials. Extension of the substrate scope of the pronucleophile from indoles to pyrroles and electron-rich arenes was realized. Additionally, methoxyphenylation is not limited to THIQ but can be carried out on isochroman as well, again employing iron and copper catalysis. American Chemical Society 2011-09-09 2011-11-04 /pmc/articles/PMC3226323/ /pubmed/21902275 http://dx.doi.org/10.1021/jo201511d Text en Copyright © 2011 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Ghobrial, Michael
Schnürch, Michael
Mihovilovic, Marko D.
Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
title Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
title_full Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
title_fullStr Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
title_full_unstemmed Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
title_short Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
title_sort direct functionalization of (un)protected tetrahydroisoquinoline and isochroman under iron and copper catalysis: two metals, two mechanisms
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3226323/
https://www.ncbi.nlm.nih.gov/pubmed/21902275
http://dx.doi.org/10.1021/jo201511d
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AT mihovilovicmarkod directfunctionalizationofunprotectedtetrahydroisoquinolineandisochromanunderironandcoppercatalysistwometalstwomechanisms

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