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Lang SB, Locascio TM, Tunge JA. Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles. Org Lett. 2014;16(16):4308-11doi: 10.1021/ol502023d.
Lang, S. B., Locascio, T. M., & Tunge, J. A. (2014). Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles. Organic letters, 16(16), 4308-11. https://doi.org/10.1021/ol502023d
Lang, Simon B, et al. "Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles." Organic letters vol. 16,16 (2014): 4308-11. doi: https://doi.org/10.1021/ol502023d
Lang SB, Locascio TM, Tunge JA. Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles. Org Lett. 2014 Aug 15;16(16):4308-11. doi: 10.1021/ol502023d. Epub 2014 Aug 04. PMID: 25089846; PMCID: PMC4136682.
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Org Lett. 2014 Aug 15;16(16):4308-11. doi: 10.1021/ol502023d. Epub 2014 Aug 04.

Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles.

Organic letters

Simon B Lang, Theresa M Locascio, Jon A Tunge

Affiliations

  1. Department of Chemistry, The University of Kansas , 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.

PMID: 25089846 PMCID: PMC4136682 DOI: 10.1021/ol502023d

Abstract

The direct coupling of allyl alcohols with nitroalkanes, nitriles, and aldehydes using catalytic Pd(PPh3)4 has been accomplished via activation of C-OH bonds with CO2. The in situ formation of carbonates from alcohols and CO2 facilitates oxidative addition to Pd to form reactive π-allylpalladium intermediates. In addition, the formation of a strong base activates nucleophiles toward the reaction with the π-allylpalladium electrophile. Overall, this atom economical reaction provides a new C-C bond without the use of an external base and generates water as the only byproduct.

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