Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones

[Image: see text] A dynamic kinetic asymmetric Pd-catalyzed cross-coupling reaction of heterobiaryl bromides with ketone N-tosylhydrazones for the synthesis of heterobiaryl styrenes is described. The combination of Pd(dba)(2) as a precatalyst with a TADDOL-derived phosphoramidite ligand provides the...

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Autores principales: Kattela, Shivashankar, Roque D. Correia, Carlos, Ros, Abel, Hornillos, Valentín, Iglesias-Sigüenza, Javier, Fernández, Rosario, Lassaletta, José M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490869/
https://www.ncbi.nlm.nih.gov/pubmed/35604334
http://dx.doi.org/10.1021/acs.orglett.2c01355
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author Kattela, Shivashankar
Roque D. Correia, Carlos
Ros, Abel
Hornillos, Valentín
Iglesias-Sigüenza, Javier
Fernández, Rosario
Lassaletta, José M.
author_facet Kattela, Shivashankar
Roque D. Correia, Carlos
Ros, Abel
Hornillos, Valentín
Iglesias-Sigüenza, Javier
Fernández, Rosario
Lassaletta, José M.
author_sort Kattela, Shivashankar
collection PubMed
description [Image: see text] A dynamic kinetic asymmetric Pd-catalyzed cross-coupling reaction of heterobiaryl bromides with ketone N-tosylhydrazones for the synthesis of heterobiaryl styrenes is described. The combination of Pd(dba)(2) as a precatalyst with a TADDOL-derived phosphoramidite ligand provides the corresponding coupling products in good yields and high enantioselectivities under mild conditions. Racemization-free N-oxidation and N-alkylation of the products allowed us to obtain appealing functionalized axially chiral heterobiaryl derivatives.
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spelling pubmed-94908692022-09-22 Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones Kattela, Shivashankar Roque D. Correia, Carlos Ros, Abel Hornillos, Valentín Iglesias-Sigüenza, Javier Fernández, Rosario Lassaletta, José M. Org Lett [Image: see text] A dynamic kinetic asymmetric Pd-catalyzed cross-coupling reaction of heterobiaryl bromides with ketone N-tosylhydrazones for the synthesis of heterobiaryl styrenes is described. The combination of Pd(dba)(2) as a precatalyst with a TADDOL-derived phosphoramidite ligand provides the corresponding coupling products in good yields and high enantioselectivities under mild conditions. Racemization-free N-oxidation and N-alkylation of the products allowed us to obtain appealing functionalized axially chiral heterobiaryl derivatives. American Chemical Society 2022-05-23 2022-06-03 /pmc/articles/PMC9490869/ /pubmed/35604334 http://dx.doi.org/10.1021/acs.orglett.2c01355 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 Kattela, Shivashankar
Roque D. Correia, Carlos
Ros, Abel
Hornillos, Valentín
Iglesias-Sigüenza, Javier
Fernández, Rosario
Lassaletta, José M.
Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones
title Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones
title_full Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones
title_fullStr Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones
title_full_unstemmed Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones
title_short Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones
title_sort pd-catalyzed dynamic kinetic asymmetric cross-coupling of heterobiaryl bromides with n-tosylhydrazones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490869/
https://www.ncbi.nlm.nih.gov/pubmed/35604334
http://dx.doi.org/10.1021/acs.orglett.2c01355
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