Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes

[Image: see text] Yndiamides offer opportunities for the synthesis of vicinally nitrogen-disubstituted aromatics and azacycles. Here we report the Rh-catalyzed cyclotrimerization of alkynyl yndiamides with alkynes, the regiochemical outcome of which is controlled by the electronic properties of the...

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Autores principales: Smith, Philip J., Tong, Zixuan, Ragus, Julia, Solon, Pearse, Shimkin, Kirk W., Anderson, Edward A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9594354/
https://www.ncbi.nlm.nih.gov/pubmed/36214595
http://dx.doi.org/10.1021/acs.orglett.2c02770
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author Smith, Philip J.
Tong, Zixuan
Ragus, Julia
Solon, Pearse
Shimkin, Kirk W.
Anderson, Edward A.
author_facet Smith, Philip J.
Tong, Zixuan
Ragus, Julia
Solon, Pearse
Shimkin, Kirk W.
Anderson, Edward A.
author_sort Smith, Philip J.
collection PubMed
description [Image: see text] Yndiamides offer opportunities for the synthesis of vicinally nitrogen-disubstituted aromatics and azacycles. Here we report the Rh-catalyzed cyclotrimerization of alkynyl yndiamides with alkynes, the regiochemical outcome of which is controlled by the electronic properties of the alkyne partner, enabling the formation of 7-aminoindolines with excellent selectivity (up to >20:1 r.r.). We also report a complementary synthesis of bicyclic 1,2-dianiline derivatives by cyclotrimerization of yndiamides with terminal diynes, where slow addition of the diyne overcomes self-dimerization.
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spelling pubmed-95943542022-10-26 Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes Smith, Philip J. Tong, Zixuan Ragus, Julia Solon, Pearse Shimkin, Kirk W. Anderson, Edward A. Org Lett [Image: see text] Yndiamides offer opportunities for the synthesis of vicinally nitrogen-disubstituted aromatics and azacycles. Here we report the Rh-catalyzed cyclotrimerization of alkynyl yndiamides with alkynes, the regiochemical outcome of which is controlled by the electronic properties of the alkyne partner, enabling the formation of 7-aminoindolines with excellent selectivity (up to >20:1 r.r.). We also report a complementary synthesis of bicyclic 1,2-dianiline derivatives by cyclotrimerization of yndiamides with terminal diynes, where slow addition of the diyne overcomes self-dimerization. American Chemical Society 2022-10-10 2022-10-21 /pmc/articles/PMC9594354/ /pubmed/36214595 http://dx.doi.org/10.1021/acs.orglett.2c02770 Text en © 2022 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 Smith, Philip J.
Tong, Zixuan
Ragus, Julia
Solon, Pearse
Shimkin, Kirk W.
Anderson, Edward A.
Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes
title Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes
title_full Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes
title_fullStr Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes
title_full_unstemmed Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes
title_short Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerizations of Yndiamides with Alkynes
title_sort rhodium-catalyzed [2 + 2 + 2] cyclotrimerizations of yndiamides with alkynes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9594354/
https://www.ncbi.nlm.nih.gov/pubmed/36214595
http://dx.doi.org/10.1021/acs.orglett.2c02770
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