Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds

A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can...

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Autores principales: Derosa, Joseph, van der Puyl, Vincent A., Tran, Van T., Liu, Mingyu, Engle, Keary M.
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/PMC6001383/
https://www.ncbi.nlm.nih.gov/pubmed/29997883
http://dx.doi.org/10.1039/c8sc01735b
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author Derosa, Joseph
van der Puyl, Vincent A.
Tran, Van T.
Liu, Mingyu
Engle, Keary M.
author_facet Derosa, Joseph
van der Puyl, Vincent A.
Tran, Van T.
Liu, Mingyu
Engle, Keary M.
author_sort Derosa, Joseph
collection PubMed
description A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.
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spelling pubmed-60013832018-07-11 Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds Derosa, Joseph van der Puyl, Vincent A. Tran, Van T. Liu, Mingyu Engle, Keary M. Chem Sci Chemistry A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments. Royal Society of Chemistry 2018-05-16 /pmc/articles/PMC6001383/ /pubmed/29997883 http://dx.doi.org/10.1039/c8sc01735b Text en This journal is © The Royal Society of Chemistry 2018 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
Derosa, Joseph
van der Puyl, Vincent A.
Tran, Van T.
Liu, Mingyu
Engle, Keary M.
Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
title Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
title_full Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
title_fullStr Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
title_full_unstemmed Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
title_short Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
title_sort directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6001383/
https://www.ncbi.nlm.nih.gov/pubmed/29997883
http://dx.doi.org/10.1039/c8sc01735b
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AT liumingyu directednickelcatalyzed12dialkylationofalkenylcarbonylcompounds
AT englekearym directednickelcatalyzed12dialkylationofalkenylcarbonylcompounds

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