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Hydroarylation of alkynes catalyzed by nickel.
Chem Rec. 2011 Sep; 11(5):242-51.CR

Abstract

Nickel catalysts derived from bis(1,5-cyclooctadiene)nickel [Ni(cod)(2)] and trialkylphosphines effect hydroarylation of alkynes through functionalization of C-H bonds of arenes including benzo-fused five-membered heteroarenes, pyridine-N-oxides, pyridines, 2-pyridones, and perfluoroarenes. The reactions proceed with excellent stereo- and regioselectivity to give disubstituted arylethenes in good yields. Use of Lewis acid (LA) co-catalysts is crucial for success in reactions of imidazoles, pyridines, and 2-pyridones; it is possible that coordination of the LA to the nitrogen or oxygen functionalities of such substrates increases the reactivity of their C-H bonds towards nickel(0) species.

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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

MeSH

AlkynesCatalysisEthylenesMolecular StructureNickelOrganometallic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21898779

Citation

Nakao, Yoshiaki. "Hydroarylation of Alkynes Catalyzed By Nickel." Chemical Record (New York, N.Y.), vol. 11, no. 5, 2011, pp. 242-51.
Nakao Y. Hydroarylation of alkynes catalyzed by nickel. Chem Rec. 2011;11(5):242-51.
Nakao, Y. (2011). Hydroarylation of alkynes catalyzed by nickel. Chemical Record (New York, N.Y.), 11(5), 242-51. https://doi.org/10.1002/tcr.201100023
Nakao Y. Hydroarylation of Alkynes Catalyzed By Nickel. Chem Rec. 2011;11(5):242-51. PubMed PMID: 21898779.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydroarylation of alkynes catalyzed by nickel. A1 - Nakao,Yoshiaki, Y1 - 2011/09/06/ PY - 2011/07/27/received PY - 2011/9/8/entrez PY - 2011/9/8/pubmed PY - 2012/1/14/medline SP - 242 EP - 51 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 11 IS - 5 N2 - Nickel catalysts derived from bis(1,5-cyclooctadiene)nickel [Ni(cod)(2)] and trialkylphosphines effect hydroarylation of alkynes through functionalization of C-H bonds of arenes including benzo-fused five-membered heteroarenes, pyridine-N-oxides, pyridines, 2-pyridones, and perfluoroarenes. The reactions proceed with excellent stereo- and regioselectivity to give disubstituted arylethenes in good yields. Use of Lewis acid (LA) co-catalysts is crucial for success in reactions of imidazoles, pyridines, and 2-pyridones; it is possible that coordination of the LA to the nitrogen or oxygen functionalities of such substrates increases the reactivity of their C-H bonds towards nickel(0) species. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/21898779/Hydroarylation_of_alkynes_catalyzed_by_nickel_ L2 - https://doi.org/10.1002/tcr.201100023 DB - PRIME DP - Unbound Medicine ER -