Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers

[Image: see text] Conjugate addition of organometallic reagents to enones to form silyl enol ether products is a versatile method to difunctionalize activated olefins, but the organometallic reagents required can be limiting. The reductive cross-electrophile coupling of unhindered primary alkyl brom...

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Autores principales: Huihui, Kierra M. M., Shrestha, Ruja, Weix, Daniel J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5260806/
https://www.ncbi.nlm.nih.gov/pubmed/28054785
http://dx.doi.org/10.1021/acs.orglett.6b03509
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author Huihui, Kierra M. M.
Shrestha, Ruja
Weix, Daniel J.
author_facet Huihui, Kierra M. M.
Shrestha, Ruja
Weix, Daniel J.
author_sort Huihui, Kierra M. M.
collection PubMed
description [Image: see text] Conjugate addition of organometallic reagents to enones to form silyl enol ether products is a versatile method to difunctionalize activated olefins, but the organometallic reagents required can be limiting. The reductive cross-electrophile coupling of unhindered primary alkyl bromides with enones and chlorosilanes to form silyl enol ether products is catalyzed by a nickel-complexed ortho-brominated terpyridine ligand. The conditions are compatible with a variety of cyclic/acyclic enones and functional groups.
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spelling pubmed-52608062018-01-05 Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers Huihui, Kierra M. M. Shrestha, Ruja Weix, Daniel J. Org Lett [Image: see text] Conjugate addition of organometallic reagents to enones to form silyl enol ether products is a versatile method to difunctionalize activated olefins, but the organometallic reagents required can be limiting. The reductive cross-electrophile coupling of unhindered primary alkyl bromides with enones and chlorosilanes to form silyl enol ether products is catalyzed by a nickel-complexed ortho-brominated terpyridine ligand. The conditions are compatible with a variety of cyclic/acyclic enones and functional groups. American Chemical Society 2017-01-05 2017-01-20 /pmc/articles/PMC5260806/ /pubmed/28054785 http://dx.doi.org/10.1021/acs.orglett.6b03509 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Huihui, Kierra M. M.
Shrestha, Ruja
Weix, Daniel J.
Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers
title Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers
title_full Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers
title_fullStr Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers
title_full_unstemmed Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers
title_short Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers
title_sort nickel-catalyzed reductive conjugate addition of primary alkyl bromides to enones to form silyl enol ethers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5260806/
https://www.ncbi.nlm.nih.gov/pubmed/28054785
http://dx.doi.org/10.1021/acs.orglett.6b03509
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AT shrestharuja nickelcatalyzedreductiveconjugateadditionofprimaryalkylbromidestoenonestoformsilylenolethers
AT weixdanielj nickelcatalyzedreductiveconjugateadditionofprimaryalkylbromidestoenonestoformsilylenolethers

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