Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

Ghina’a I. Abu Deiab; Mohammed H. Al-Huniti; I. F. Dempsey Hyatt; Emma E. Nagy; Kristen E. Gettys; Sommayah S. Sayed; Christine M. Joliat; Paige E. Daniel; Rupa M. Vummalaneni; Andrew T. Morehead Jr; Andrew L. Sargent; Mitchell P. Croatt

doi:10.3762/bjoc.13.41

Beilstein Journal of Organic Chemistry (Feb 2017)

Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

Ghina’a I. Abu Deiab,
Mohammed H. Al-Huniti,
I. F. Dempsey Hyatt,
Emma E. Nagy,
Kristen E. Gettys,
Sommayah S. Sayed,
Christine M. Joliat,
Paige E. Daniel,
Rupa M. Vummalaneni,
Andrew T. Morehead Jr,
Andrew L. Sargent,
Mitchell P. Croatt

Affiliations

Ghina’a I. Abu Deiab: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Mohammed H. Al-Huniti: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
I. F. Dempsey Hyatt: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Emma E. Nagy: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Kristen E. Gettys: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Sommayah S. Sayed: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Christine M. Joliat: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Paige E. Daniel: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Rupa M. Vummalaneni: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA
Andrew T. Morehead Jr: Department of Chemistry, East Carolina University, Greenville, NC 27858, USA
Andrew L. Sargent: Department of Chemistry, East Carolina University, Greenville, NC 27858, USA
Mitchell P. Croatt: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA

DOI: https://doi.org/10.3762/bjoc.13.41
Journal volume & issue: Vol. 13, no. 1
pp. 384 – 392

Abstract

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Dienoic acids and pentadienyl alcohols are coupled in a decarboxylative and dehydrative manner at ambient temperature using Pd(0) catalysis to generate 1,3,6,8-tetraenes. Contrary to related decarboxylative coupling reactions, an anion-stabilizing group is not required adjacent to the carboxyl group. Of mechanistic importance, it appears that both the diene of the acid and the diene of the alcohol are required for this reaction. To further understand this reaction, substitutions at every unique position of both coupling partners was examined and two potential mechanisms are presented.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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Abstract

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