Journal of the American Chemical Society, volume 136, issue 18, pages 6586-6589
Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1,3-Diols
Publication type: Journal Article
Publication date: 2014-04-22
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We report Ir-catalyzed intramolecular silylation of secondary alkyl C-H bonds. (Hydrido)silyl ethers, generated in situ by dehydrogenative coupling of a tertiary or conformationally restricted secondary alcohol with diethylsilane, undergo regioselective silylation at a secondary C-H bond γ to the hydroxyl group. Oxidation of the resulting oxasilolanes in the same vessel generates 1,3-diols. This method provides a strategy to synthesize 1,3-diols through a hydroxyl-directed, functionalization of secondary alkyl C-H bonds. Mechanistic studies suggest that the C-H bond cleavage is the turnover-limiting step of the catalytic cycle. This silylation of secondary C-H bonds is only 40-50 times slower than the analogous silylation of primary C-H bonds.
Top-30
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3 publications, 2.33%
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3 publications, 2.33%
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2 publications, 1.55%
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2 publications, 1.55%
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2 publications, 1.55%
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2 publications, 1.55%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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1 publication, 0.78%
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ACS Central Science
1 publication, 0.78%
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Citations by publishers
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American Chemical Society (ACS)
48 publications, 37.21%
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Wiley
44 publications, 34.11%
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Royal Society of Chemistry (RSC)
13 publications, 10.08%
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Elsevier
8 publications, 6.2%
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Springer Nature
7 publications, 5.43%
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Thieme
3 publications, 2.33%
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The Chemical Society of Japan
1 publication, 0.78%
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Canadian Science Publishing
1 publication, 0.78%
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Shanghai Institute of Organic Chemistry
1 publication, 0.78%
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Society of Synthetic Organic Chemistry
1 publication, 0.78%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 0.78%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.78%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Li B. et al. Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1,3-Diols // Journal of the American Chemical Society. 2014. Vol. 136. No. 18. pp. 6586-6589.
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Li B., Driess M., Hartwig J. H. Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1,3-Diols // Journal of the American Chemical Society. 2014. Vol. 136. No. 18. pp. 6586-6589.
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TY - JOUR
DO - 10.1021/ja5026479
UR - https://doi.org/10.1021/ja5026479
TI - Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1,3-Diols
T2 - Journal of the American Chemical Society
AU - Li, Bijie
AU - Driess, Matthias
AU - Hartwig, John H
PY - 2014
DA - 2014/04/22 00:00:00
PB - American Chemical Society (ACS)
SP - 6586-6589
IS - 18
VL - 136
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
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@article{2014_Li,
author = {Bijie Li and Matthias Driess and John H Hartwig},
title = {Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1,3-Diols},
journal = {Journal of the American Chemical Society},
year = {2014},
volume = {136},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ja5026479},
number = {18},
pages = {6586--6589},
doi = {10.1021/ja5026479}
}
Cite this
MLA
Copy
Li, Bijie, et al. “Iridium-Catalyzed Regioselective Silylation of Secondary Alkyl C–H Bonds for the Synthesis of 1,3-Diols.” Journal of the American Chemical Society, vol. 136, no. 18, Apr. 2014, pp. 6586-6589. https://doi.org/10.1021/ja5026479.