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N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles
Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, we explore redox-active carb...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8101283/ https://www.ncbi.nlm.nih.gov/pubmed/33956022 http://dx.doi.org/10.1039/d1cc01026c |
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author | Chowdhury, Rajdip Mendoza, Abraham |
author_facet | Chowdhury, Rajdip Mendoza, Abraham |
author_sort | Chowdhury, Rajdip |
collection | PubMed |
description | Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, we explore redox-active carbenes in the expedited and divergent synthesis of functionalized indoles. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions. |
format | Online Article Text |
id | pubmed-8101283 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81012832021-05-13 N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles Chowdhury, Rajdip Mendoza, Abraham Chem Commun (Camb) Chemistry Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, we explore redox-active carbenes in the expedited and divergent synthesis of functionalized indoles. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions. The Royal Society of Chemistry 2021-03-29 /pmc/articles/PMC8101283/ /pubmed/33956022 http://dx.doi.org/10.1039/d1cc01026c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Chowdhury, Rajdip Mendoza, Abraham N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles |
title |
N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles |
title_full |
N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles |
title_fullStr |
N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles |
title_full_unstemmed |
N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles |
title_short |
N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles |
title_sort | n-hydroxyphthalimidyl diazoacetate (nhpi-da): a modular methylene linchpin for the c–h alkylation of indoles |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8101283/ https://www.ncbi.nlm.nih.gov/pubmed/33956022 http://dx.doi.org/10.1039/d1cc01026c |
work_keys_str_mv | AT chowdhuryrajdip nhydroxyphthalimidyldiazoacetatenhpidaamodularmethylenelinchpinforthechalkylationofindoles AT mendozaabraham nhydroxyphthalimidyldiazoacetatenhpidaamodularmethylenelinchpinforthechalkylationofindoles |