Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO
Sophia M. Baldassarre
1
,
Heidi S. Sato
1
,
Hiroyuki Sato
1
,
Adam P. Louise
1
,
Layna L. Summer
1
,
Benjamin P. Wilson
1
,
Brett N Hemric
1
1
Department of Chemistry and Biochemistry, University of Tampa, Tampa, Florida 33606, United States
|
Publication type: Journal Article
Publication date: 2024-11-04
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
39492589
Abstract
A mild, metal-free 1,2-dioxygenation of 1,3-dienes using TEMPO and carboxylic acids is reported. This method includes examples for a variety of 1,3-dienes as well as aliphatic and aromatic carboxylic acids. This reaction also demonstrates complete site- and regioselectivity in the oxygen addition. Furthermore, extensive derivatization of the differential oxygen groups in the product has been demonstrated, including reduction of the remaining alkene to access alkyl, vicinally dioxygenated scaffolds. Finally, this reaction is shown both experimentally and computationally to occur through carboxylic acid-driven disproportionation of TEMPO.
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Baldassarre S. M. et al. Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO // Journal of Organic Chemistry. 2024. Vol. 89. No. 22. pp. 16865-16872.
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Baldassarre S. M., Sato H. S., Sato H., Louise A. P., Summer L. L., Wilson B. P., Hemric B. N. Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO // Journal of Organic Chemistry. 2024. Vol. 89. No. 22. pp. 16865-16872.
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TY - JOUR
DO - 10.1021/acs.joc.4c02244
UR - https://pubs.acs.org/doi/10.1021/acs.joc.4c02244
TI - Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO
T2 - Journal of Organic Chemistry
AU - Baldassarre, Sophia M.
AU - Sato, Heidi S.
AU - Sato, Hiroyuki
AU - Louise, Adam P.
AU - Summer, Layna L.
AU - Wilson, Benjamin P.
AU - Hemric, Brett N
PY - 2024
DA - 2024/11/04
PB - American Chemical Society (ACS)
SP - 16865-16872
IS - 22
VL - 89
PMID - 39492589
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2024_Baldassarre,
author = {Sophia M. Baldassarre and Heidi S. Sato and Hiroyuki Sato and Adam P. Louise and Layna L. Summer and Benjamin P. Wilson and Brett N Hemric},
title = {Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO},
journal = {Journal of Organic Chemistry},
year = {2024},
volume = {89},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.4c02244},
number = {22},
pages = {16865--16872},
doi = {10.1021/acs.joc.4c02244}
}
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MLA
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Baldassarre, Sophia M., et al. “Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO.” Journal of Organic Chemistry, vol. 89, no. 22, Nov. 2024, pp. 16865-16872. https://pubs.acs.org/doi/10.1021/acs.joc.4c02244.