Advanced Synthesis and Catalysis, volume 355, issue 4, pages 697-704

Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols

Qing Xu
Quan Liu
Publication typeJournal Article
Publication date2013-02-22
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.4
ISSN16154150, 16154169
General Chemistry
Abstract
Different to the borrowing hydrogen strategy in which alcohols were activated by transition metal-catalyzed anaerobic dehydrogenation, the direct addition of aldehydes was found to be an effective but simpler way of alcohol activation that can lead to efficient and green aldehyde-catalyzed transition metal-free dehydrative C-alkylation of methyl carbinols with alcohols. Mechanistic studies revealed that the reaction proceeds via in situ formation of ketones by Oppenauer oxidation of the methyl carbinols by external aldehydes, aldol condensation, and Meerwein–Ponndorf–Verley (MPV)-type reduction of α,β-unsatutated ketones by substrate alcohols, affording the useful long chain alcohols and generating aldehydes and ketones as the by-products that will be recovered in the next condensation to finish the catalytic cycle.

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GOST |
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GOST Copy
Xu Q., Chen J., Liu Q. Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols // Advanced Synthesis and Catalysis. 2013. Vol. 355. No. 4. pp. 697-704.
GOST all authors (up to 50) Copy
Xu Q., Chen J., Liu Q. Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols // Advanced Synthesis and Catalysis. 2013. Vol. 355. No. 4. pp. 697-704.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/adsc.201200996
UR - https://doi.org/10.1002/adsc.201200996
TI - Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols
T2 - Advanced Synthesis and Catalysis
AU - Xu, Qing
AU - Chen, Jianhui
AU - Liu, Quan
PY - 2013
DA - 2013/02/22 00:00:00
PB - Wiley
SP - 697-704
IS - 4
VL - 355
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
Cite this
BibTex Copy
@article{2013_Xu,
author = {Qing Xu and Jianhui Chen and Quan Liu},
title = {Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols},
journal = {Advanced Synthesis and Catalysis},
year = {2013},
volume = {355},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/adsc.201200996},
number = {4},
pages = {697--704},
doi = {10.1002/adsc.201200996}
}
MLA
Cite this
MLA Copy
Xu, Qing, et al. “Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols.” Advanced Synthesis and Catalysis, vol. 355, no. 4, Feb. 2013, pp. 697-704. https://doi.org/10.1002/adsc.201200996.
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