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Selective C-4 alkylation of pyridine by nickel/Lewis acid catalysis.
J Am Chem Soc. 2010 Oct 06; 132(39):13666-8.JA

Abstract

Direct C-4-selective addition of pyridine across alkenes and alkynes is achieved for the first time by nickel/Lewis acid cooperative catalysis with an N-heterocyclic carbene ligand. A variety of substituents on both alkenes and pyridine are tolerated to give linear 4-alkylpyridines in modest to good yields. The addition across styrene, on the other hand, gives branched 4-alkylpyridines. A single example of C-4-selective alkenylation is also described.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nakao Y
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan. yoshiakinakao@npc05.mbox.media.kyoto-u.ac.jp
Yamada Y
No affiliation info available
Kashihara N
No affiliation info available
Hiyama T
No affiliation info available

MeSH

AcidsAlkenesAlkylationAlkynesCatalysisLigandsMolecular StructureNickelOrganometallic CompoundsPyridinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20822182

Citation

Nakao, Yoshiaki, et al. "Selective C-4 Alkylation of Pyridine By nickel/Lewis Acid Catalysis." Journal of the American Chemical Society, vol. 132, no. 39, 2010, pp. 13666-8.
Nakao Y, Yamada Y, Kashihara N, et al. Selective C-4 alkylation of pyridine by nickel/Lewis acid catalysis. J Am Chem Soc. 2010;132(39):13666-8.
Nakao, Y., Yamada, Y., Kashihara, N., & Hiyama, T. (2010). Selective C-4 alkylation of pyridine by nickel/Lewis acid catalysis. Journal of the American Chemical Society, 132(39), 13666-8. https://doi.org/10.1021/ja106514b
Nakao Y, et al. Selective C-4 Alkylation of Pyridine By nickel/Lewis Acid Catalysis. J Am Chem Soc. 2010 Oct 6;132(39):13666-8. PubMed PMID: 20822182.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Selective C-4 alkylation of pyridine by nickel/Lewis acid catalysis. AU - Nakao,Yoshiaki, AU - Yamada,Yuuya, AU - Kashihara,Natsuko, AU - Hiyama,Tamejiro, PY - 2010/9/9/entrez PY - 2010/9/9/pubmed PY - 2011/1/21/medline SP - 13666 EP - 8 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 39 N2 - Direct C-4-selective addition of pyridine across alkenes and alkynes is achieved for the first time by nickel/Lewis acid cooperative catalysis with an N-heterocyclic carbene ligand. A variety of substituents on both alkenes and pyridine are tolerated to give linear 4-alkylpyridines in modest to good yields. The addition across styrene, on the other hand, gives branched 4-alkylpyridines. A single example of C-4-selective alkenylation is also described. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20822182/Selective_C_4_alkylation_of_pyridine_by_nickel/Lewis_acid_catalysis_ L2 - https://doi.org/10.1021/ja106514b DB - PRIME DP - Unbound Medicine ER -