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Wagner F, Harms K, Koert U. Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes. Org Lett. 2015;17(22):5670-3doi: 10.1021/acs.orglett.5b02952.
Wagner, F., Harms, K., & Koert, U. (2015). Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes. Organic letters, 17(22), 5670-3. https://doi.org/10.1021/acs.orglett.5b02952
Wagner, Frederic, et al. "Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes." Organic letters vol. 17,22 (2015): 5670-3. doi: https://doi.org/10.1021/acs.orglett.5b02952
Wagner F, Harms K, Koert U. Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes. Org Lett. 2015 Nov 20;17(22):5670-3. doi: 10.1021/acs.orglett.5b02952. Epub 2015 Nov 04. PMID: 26536142.
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Org Lett. 2015 Nov 20;17(22):5670-3. doi: 10.1021/acs.orglett.5b02952. Epub 2015 Nov 04.

Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes.

Organic letters

Frederic Wagner, Klaus Harms, Ulrich Koert

Affiliations

  1. Fachbereich Chemie, Philipps-University Marburg , Hans-Meerwein-Strasse 4, D-35043 Marburg, Germany.

PMID: 26536142 DOI: 10.1021/acs.orglett.5b02952

Abstract

γ-Aryl-β-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)2/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of γ-(hetero)aryl-β-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser-Heck combination. γ-Aryl-β-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 °C provides optimal conditions for this deprotective aromatization.

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