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Dorn SC, Olsen AK, Kelemen RE, et al. Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides. Tetrahedron Lett. 2015;56(23):3365-3367doi: 10.1016/j.tetlet.2015.02.120.
Dorn, S. C., Olsen, A. K., Kelemen, R. E., Shrestha, R., & Weix, D. J. (2015). Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides. Tetrahedron letters, 56(23), 3365-3367. https://doi.org/10.1016/j.tetlet.2015.02.120
Dorn, Stephanie C M, et al. "Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides." Tetrahedron letters vol. 56,23 (2015): 3365-3367. doi: https://doi.org/10.1016/j.tetlet.2015.02.120
Dorn SC, Olsen AK, Kelemen RE, Shrestha R, Weix DJ. Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides. Tetrahedron Lett. 2015 Jun 03;56(23):3365-3367. doi: 10.1016/j.tetlet.2015.02.120. PMID: 26028781; PMCID: PMC4446700.
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Tetrahedron Lett. 2015 Jun 03;56(23):3365-3367. doi: 10.1016/j.tetlet.2015.02.120.

Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides.

Tetrahedron letters

Stephanie C M Dorn, Andrew K Olsen, Rachel E Kelemen, Ruja Shrestha, Daniel J Weix

Affiliations

  1. Department of Chemistry, University of Rochester, 120 Trustee Road, Rochester, NY 14627, USA.

PMID: 26028781 PMCID: PMC4446700 DOI: 10.1016/j.tetlet.2015.02.120

Abstract

The direct, regioselective, and stereoselective arylation of activated alkynes with aryl iodides using a nickel catalyst and manganese reductant is described. The reaction conditions are mild (40 °C in MeOH, no acid or base) and an intermediate organomanganese reagent is unlikely. Functional groups tolerated include halides and pseudohalides, free and protected anilines, and a benzyl alcohol. Other activated alkynes including an amide and a ketone also reacted to form arylated products in good yields.

Keywords: alkyne; arylation; catalyzed; nickel; reductive

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