B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles

[Image: see text] The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C–H bonds in amines, we have developed a catalytic approa...

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Autores principales: Basak, Shyam, Alvarez-Montoya, Ana, Winfrey, Laura, Melen, Rebecca L., Morrill, Louis C., Pulis, Alexander P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7311048/
https://www.ncbi.nlm.nih.gov/pubmed/32596025
http://dx.doi.org/10.1021/acscatal.0c01141
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author Basak, Shyam
Alvarez-Montoya, Ana
Winfrey, Laura
Melen, Rebecca L.
Morrill, Louis C.
Pulis, Alexander P.
author_facet Basak, Shyam
Alvarez-Montoya, Ana
Winfrey, Laura
Melen, Rebecca L.
Morrill, Louis C.
Pulis, Alexander P.
author_sort Basak, Shyam
collection PubMed
description [Image: see text] The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C–H bonds in amines, we have developed a catalytic approach for the direct C3 alkylation of a wide range of indoles and oxindoles using amine-based alkylating agents. We also employed this borane-catalyzed strategy in an alkylation-ring opening cascade.
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spelling pubmed-73110482020-06-24 B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles Basak, Shyam Alvarez-Montoya, Ana Winfrey, Laura Melen, Rebecca L. Morrill, Louis C. Pulis, Alexander P. ACS Catal [Image: see text] The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C–H bonds in amines, we have developed a catalytic approach for the direct C3 alkylation of a wide range of indoles and oxindoles using amine-based alkylating agents. We also employed this borane-catalyzed strategy in an alkylation-ring opening cascade. American Chemical Society 2020-04-09 2020-04-17 /pmc/articles/PMC7311048/ /pubmed/32596025 http://dx.doi.org/10.1021/acscatal.0c01141 Text en Copyright © 2020 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 Basak, Shyam
Alvarez-Montoya, Ana
Winfrey, Laura
Melen, Rebecca L.
Morrill, Louis C.
Pulis, Alexander P.
B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
title B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
title_full B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
title_fullStr B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
title_full_unstemmed B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
title_short B(C(6)F(5))(3)-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
title_sort b(c(6)f(5))(3)-catalyzed direct c3 alkylation of indoles and oxindoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7311048/
https://www.ncbi.nlm.nih.gov/pubmed/32596025
http://dx.doi.org/10.1021/acscatal.0c01141
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