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Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory

[Image: see text] A modern undergraduate organic chemistry laboratory experiment involving the Suzuki–Miyaura coupling is reported. Although Suzuki–Miyaura couplings typically employ palladium catalysts in environmentally harmful solvents, this experiment features the use of inexpensive nickel catal...

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Autores principales: Hie, Liana, Chang, Jonah J., Garg, Neil K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and Division of Chemical Education, Inc. 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4354682/
https://www.ncbi.nlm.nih.gov/pubmed/25774064
http://dx.doi.org/10.1021/ed500158p
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author Hie, Liana
Chang, Jonah J.
Garg, Neil K.
author_facet Hie, Liana
Chang, Jonah J.
Garg, Neil K.
author_sort Hie, Liana
collection PubMed
description [Image: see text] A modern undergraduate organic chemistry laboratory experiment involving the Suzuki–Miyaura coupling is reported. Although Suzuki–Miyaura couplings typically employ palladium catalysts in environmentally harmful solvents, this experiment features the use of inexpensive nickel catalysis, in addition to a “green” alcohol solvent. The experiment employs heterocyclic substrates, which are important pharmaceutical building blocks. Thus, this laboratory procedure exposes students to a variety of contemporary topics in organic chemistry, including transition metal-catalyzed cross-couplings, green chemistry, and the importance of heterocycles in drug discovery, none of which are well represented in typical undergraduate organic chemistry curricula. The experimental protocol uses commercially available reagents and is useful in both organic and inorganic instructional laboratories.
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spelling pubmed-43546822015-09-05 Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory Hie, Liana Chang, Jonah J. Garg, Neil K. J Chem Educ [Image: see text] A modern undergraduate organic chemistry laboratory experiment involving the Suzuki–Miyaura coupling is reported. Although Suzuki–Miyaura couplings typically employ palladium catalysts in environmentally harmful solvents, this experiment features the use of inexpensive nickel catalysis, in addition to a “green” alcohol solvent. The experiment employs heterocyclic substrates, which are important pharmaceutical building blocks. Thus, this laboratory procedure exposes students to a variety of contemporary topics in organic chemistry, including transition metal-catalyzed cross-couplings, green chemistry, and the importance of heterocycles in drug discovery, none of which are well represented in typical undergraduate organic chemistry curricula. The experimental protocol uses commercially available reagents and is useful in both organic and inorganic instructional laboratories. American Chemical Society and Division of Chemical Education, Inc. 2014-09-05 2015-03-10 /pmc/articles/PMC4354682/ /pubmed/25774064 http://dx.doi.org/10.1021/ed500158p Text en Copyright © 2014 American Chemical Society and Division of Chemical Education, Inc. 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 Hie, Liana
Chang, Jonah J.
Garg, Neil K.
Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory
title Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory
title_full Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory
title_fullStr Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory
title_full_unstemmed Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory
title_short Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory
title_sort nickel-catalyzed suzuki–miyaura cross-coupling in a green alcohol solvent for an undergraduate organic chemistry laboratory
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4354682/
https://www.ncbi.nlm.nih.gov/pubmed/25774064
http://dx.doi.org/10.1021/ed500158p
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AT gargneilk nickelcatalyzedsuzukimiyauracrosscouplinginagreenalcoholsolventforanundergraduateorganicchemistrylaboratory