Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols

[Image: see text] We report a Pd-catalyzed route to heterocycles bearing a tetrasubstituted alkene fragment. Our approach merges the intramolecular carbopalladation of tethered alkynes with an alkylation step produced by the C–C cleavage of cyclobutanol derivatives. An alkenyl-Pd(II) intermediate ha...

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Autores principales: Pérez-Gómez, Marta, Herrera-Ramírez, Piedad, Bautista, Delia, Saura-Llamas, Isabel, García-López, José-Antonio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8925021/
https://www.ncbi.nlm.nih.gov/pubmed/35308581
http://dx.doi.org/10.1021/acs.organomet.2c00015
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author Pérez-Gómez, Marta
Herrera-Ramírez, Piedad
Bautista, Delia
Saura-Llamas, Isabel
García-López, José-Antonio
author_facet Pérez-Gómez, Marta
Herrera-Ramírez, Piedad
Bautista, Delia
Saura-Llamas, Isabel
García-López, José-Antonio
author_sort Pérez-Gómez, Marta
collection PubMed
description [Image: see text] We report a Pd-catalyzed route to heterocycles bearing a tetrasubstituted alkene fragment. Our approach merges the intramolecular carbopalladation of tethered alkynes with an alkylation step produced by the C–C cleavage of cyclobutanol derivatives. An alkenyl-Pd(II) intermediate has been isolated and characterized by X-ray diffraction studies. Interestingly, the nature of the tethering alkynyl chain influences the E/Z stereochemistry of the alkenyl fragment in the functionalized heterocycles.
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spelling pubmed-89250212022-03-17 Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols Pérez-Gómez, Marta Herrera-Ramírez, Piedad Bautista, Delia Saura-Llamas, Isabel García-López, José-Antonio Organometallics [Image: see text] We report a Pd-catalyzed route to heterocycles bearing a tetrasubstituted alkene fragment. Our approach merges the intramolecular carbopalladation of tethered alkynes with an alkylation step produced by the C–C cleavage of cyclobutanol derivatives. An alkenyl-Pd(II) intermediate has been isolated and characterized by X-ray diffraction studies. Interestingly, the nature of the tethering alkynyl chain influences the E/Z stereochemistry of the alkenyl fragment in the functionalized heterocycles. American Chemical Society 2022-03-03 2022-03-14 /pmc/articles/PMC8925021/ /pubmed/35308581 http://dx.doi.org/10.1021/acs.organomet.2c00015 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 Pérez-Gómez, Marta
Herrera-Ramírez, Piedad
Bautista, Delia
Saura-Llamas, Isabel
García-López, José-Antonio
Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols
title Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols
title_full Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols
title_fullStr Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols
title_full_unstemmed Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols
title_short Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols
title_sort synthesis of benzofused o- and n-heterocycles through cascade carbopalladation/cross-alkylation of alkynes involving the c–c cleavage of cyclobutanols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8925021/
https://www.ncbi.nlm.nih.gov/pubmed/35308581
http://dx.doi.org/10.1021/acs.organomet.2c00015
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