Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination
1
Department of Chemistry, University of Richmond, 138 UR Drive, Richmond, Virginia USA 23173, United States
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Publication type: Journal Article
Publication date: 2022-10-14
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36239694
Organic Chemistry
Abstract
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine, α,α-disubstituted aldehydes condense with electron-rich aromatic aldehydes to yield β,β-disubstituted styrenes. More electron-rich aromatic aldehydes react more rapidly and in higher yield. Preliminary results suggest that the reaction may proceed via the ionization and formal deformylation of an aldol intermediate.
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Dixon G. J. et al. Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination // Journal of Organic Chemistry. 2022. Vol. 87. No. 21. pp. 14846-14854.
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Dixon G. J., Rodriguez M. R., Chong T. G., Kim K. Y., Downey C. W. Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination // Journal of Organic Chemistry. 2022. Vol. 87. No. 21. pp. 14846-14854.
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TY - JOUR
DO - 10.1021/acs.joc.2c01458
UR - https://doi.org/10.1021/acs.joc.2c01458
TI - Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination
T2 - Journal of Organic Chemistry
AU - Dixon, Grant J
AU - Rodriguez, Michael R
AU - Chong, Tyler G
AU - Kim, Kevin Y
AU - Downey, C Wade
PY - 2022
DA - 2022/10/14
PB - American Chemical Society (ACS)
SP - 14846-14854
IS - 21
VL - 87
PMID - 36239694
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Dixon,
author = {Grant J Dixon and Michael R Rodriguez and Tyler G Chong and Kevin Y Kim and C Wade Downey},
title = {Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.2c01458},
number = {21},
pages = {14846--14854},
doi = {10.1021/acs.joc.2c01458}
}
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MLA
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Dixon, Grant J., et al. “Synthesis of β,β-Disubstituted Styrenes via Trimethylsilyl Trifluoromethanesulfonate-Promoted Aldehyde-Aldehyde Aldol Coupling-Elimination.” Journal of Organic Chemistry, vol. 87, no. 21, Oct. 2022, pp. 14846-14854. https://doi.org/10.1021/acs.joc.2c01458.