Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement

An unusual γ-selectivity was observed in the arylation of γ,δ-unsaturated O-carbamates involving directed lithiation, transmetallation to zinc and Negishi coupling, when a specific combination of aryl electrophile and phosphine ligand is employed. Mechanistic studies indicate that an unusual, stereo...

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Autores principales: Royal, Titouan, Baudoin, Olivier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385668/
https://www.ncbi.nlm.nih.gov/pubmed/30881660
http://dx.doi.org/10.1039/c8sc05058a
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author Royal, Titouan
Baudoin, Olivier
author_facet Royal, Titouan
Baudoin, Olivier
author_sort Royal, Titouan
collection PubMed
description An unusual γ-selectivity was observed in the arylation of γ,δ-unsaturated O-carbamates involving directed lithiation, transmetallation to zinc and Negishi coupling, when a specific combination of aryl electrophile and phosphine ligand is employed. Mechanistic studies indicate that an unusual, stereospecific haptotropic rearrangement of the palladium–diene intermediate is involved.
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spelling pubmed-63856682019-03-15 Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement Royal, Titouan Baudoin, Olivier Chem Sci Chemistry An unusual γ-selectivity was observed in the arylation of γ,δ-unsaturated O-carbamates involving directed lithiation, transmetallation to zinc and Negishi coupling, when a specific combination of aryl electrophile and phosphine ligand is employed. Mechanistic studies indicate that an unusual, stereospecific haptotropic rearrangement of the palladium–diene intermediate is involved. Royal Society of Chemistry 2018-12-26 /pmc/articles/PMC6385668/ /pubmed/30881660 http://dx.doi.org/10.1039/c8sc05058a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Royal, Titouan
Baudoin, Olivier
Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
title Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
title_full Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
title_fullStr Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
title_full_unstemmed Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
title_short Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
title_sort pd-catalyzed γ-arylation of γ,δ-unsaturated o-carbamates via an unusual haptotropic rearrangement
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385668/
https://www.ncbi.nlm.nih.gov/pubmed/30881660
http://dx.doi.org/10.1039/c8sc05058a
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