ACS Catalysis, volume 8, issue 4, pages 3091-3103
C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts
S. M. A. Hakim Siddiki
1
,
Abeda S Touchy
1
,
Md A R Jamil
1
,
Takashi Toyao
1, 2
,
Ken-ichi Shimizu
1, 2
Publication type: Journal Article
Publication date: 2018-02-21
General Chemistry
Catalysis
Abstract
A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C–H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt–H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogen...
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Siddiki S. M. A. H. et al. C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts // ACS Catalysis. 2018. Vol. 8. No. 4. pp. 3091-3103.
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Siddiki S. M. A. H., Touchy A. S., Jamil M. A. R., Toyao T., Shimizu K. C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts // ACS Catalysis. 2018. Vol. 8. No. 4. pp. 3091-3103.
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TY - JOUR
DO - 10.1021/acscatal.7b04442
UR - https://doi.org/10.1021/acscatal.7b04442
TI - C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts
T2 - ACS Catalysis
AU - Siddiki, S. M. A. Hakim
AU - Touchy, Abeda S
AU - Jamil, Md A R
AU - Toyao, Takashi
AU - Shimizu, Ken-ichi
PY - 2018
DA - 2018/02/21
PB - American Chemical Society (ACS)
SP - 3091-3103
IS - 4
VL - 8
SN - 2155-5435
ER -
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@article{2018_Siddiki,
author = {S. M. A. Hakim Siddiki and Abeda S Touchy and Md A R Jamil and Takashi Toyao and Ken-ichi Shimizu},
title = {C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts},
journal = {ACS Catalysis},
year = {2018},
volume = {8},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acscatal.7b04442},
number = {4},
pages = {3091--3103},
doi = {10.1021/acscatal.7b04442}
}
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Siddiki, S. M. A. Hakim, et al. “C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts.” ACS Catalysis, vol. 8, no. 4, Feb. 2018, pp. 3091-3103. https://doi.org/10.1021/acscatal.7b04442.