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

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Author
Abu Deiab, Ghina’a I.; Al-Huniti, Mohammed H.; Hyatt, I. F. Dempsey; Nagy, Emma E.; Gettys, Kristen E.; Sayed, Sommayah S.; Joliat, Christine M.; Daniel, Paige E.; Vummalaneni, Rupa M.; Morehead, Andrew T. Jr.; Sargent, Andrew L.; Croatt, Mitchell P.
Abstract
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 cou- pling partners was examined and two potential mechanisms are presented.
URI
http://hdl.handle.net/10342/8171
Date
2017-02-28
Citation:
APA:
Abu Deiab, Ghina’a I., & Al-Huniti, Mohammed H., & Hyatt, I. F. Dempsey, & Nagy, Emma E., & Gettys, Kristen E., & Sayed, Sommayah S., & Joliat, Christine M., & Daniel, Paige E., & Vummalaneni, Rupa M., & Morehead, Andrew T. Jr., & Sargent, Andrew L., & Croatt, Mitchell P.. (February 2017). Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes. Beilstein Journal of Organic Chemistry, (13:1), p.384-392. Retrieved from http://hdl.handle.net/10342/8171

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MLA:
Abu Deiab, Ghina’a I., and Al-Huniti, Mohammed H., and Hyatt, I. F. Dempsey, and Nagy, Emma E., and Gettys, Kristen E., and Sayed, Sommayah S., and Joliat, Christine M., and Daniel, Paige E., and Vummalaneni, Rupa M., and Morehead, Andrew T. Jr., and Sargent, Andrew L., and Croatt, Mitchell P.. "Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes". Beilstein Journal of Organic Chemistry. 13:1. (384-392.), February 2017. September 30, 2020. http://hdl.handle.net/10342/8171.
Chicago:
Abu Deiab, Ghina’a I. and Al-Huniti, Mohammed H. and Hyatt, I. F. Dempsey and Nagy, Emma E. and Gettys, Kristen E. and Sayed, Sommayah S. and Joliat, Christine M. and Daniel, Paige E. and Vummalaneni, Rupa M. and Morehead, Andrew T. Jr. and Sargent, Andrew L. and Croatt, Mitchell P., "Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes," Beilstein Journal of Organic Chemistry 13, no. 1 (February 2017), http://hdl.handle.net/10342/8171 (accessed September 30, 2020).
AMA:
Abu Deiab, Ghina’a I., Al-Huniti, Mohammed H., Hyatt, I. F. Dempsey, Nagy, Emma E., Gettys, Kristen E., Sayed, Sommayah S., Joliat, Christine M., Daniel, Paige E., Vummalaneni, Rupa M., Morehead, Andrew T. Jr., Sargent, Andrew L., Croatt, Mitchell P.. Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes. Beilstein Journal of Organic Chemistry. February 2017; 13(1) 384-392. http://hdl.handle.net/10342/8171. Accessed September 30, 2020.
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