Nature Chemistry, volume 3, issue 4, pages 287-290
Iridium-catalysed direct C–C coupling of methanol and allenes
Publication type: Journal Article
Publication date: 2011-02-27
Journal:
Nature Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 21.8
ISSN: 17554330, 17554349
General Chemistry
General Chemical Engineering
Abstract
Methanol is an abundant (35 million metric tons per year), renewable chemical feedstock, yet its use as a one-carbon building block in fine chemical synthesis is highly underdeveloped. Using a homogeneous iridium catalyst developed in our laboratory, methanol engages in a direct C–C coupling with allenes to furnish higher alcohols that incorporate all-carbon quaternary centres, free of stoichiometric by-products. A catalytic mechanism that involves turnover-limiting methanol oxidation, a consequence of the high energetic demand of methanol dehydrogenation, is corroborated through a series of competition kinetics experiments. This process represents the first catalytic C–C coupling of methanol to provide discrete products of hydrohydroxymethylation. Methanol is an abundant, renewable chemical feedstock. Here, a homogenous iridium catalyst enables a byproduct-free C–C coupling of methanol and allenes, producing higher alcohols that incorporate all-carbon quaternary centres. This process represents the first catalytic C–C coupling of methanol to provide discrete products of hydrohydroxymethylation.
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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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Moran J. et al. Iridium-catalysed direct C–C coupling of methanol and allenes // Nature Chemistry. 2011. Vol. 3. No. 4. pp. 287-290.
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Moran J., Preetz A., Mesch R. A., Krische M. J. Iridium-catalysed direct C–C coupling of methanol and allenes // Nature Chemistry. 2011. Vol. 3. No. 4. pp. 287-290.
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TY - JOUR
DO - 10.1038/nchem.1001
UR - https://doi.org/10.1038/nchem.1001
TI - Iridium-catalysed direct C–C coupling of methanol and allenes
T2 - Nature Chemistry
AU - Moran, Joseph
AU - Preetz, Angelika
AU - Mesch, Ryan A
AU - Krische, Michael J.
PY - 2011
DA - 2011/02/27 00:00:00
PB - Springer Nature
SP - 287-290
IS - 4
VL - 3
SN - 1755-4330
SN - 1755-4349
ER -
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@article{2011_Moran,
author = {Joseph Moran and Angelika Preetz and Ryan A Mesch and Michael J. Krische},
title = {Iridium-catalysed direct C–C coupling of methanol and allenes},
journal = {Nature Chemistry},
year = {2011},
volume = {3},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1038/nchem.1001},
number = {4},
pages = {287--290},
doi = {10.1038/nchem.1001}
}
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Moran, Joseph, et al. “Iridium-catalysed direct C–C coupling of methanol and allenes.” Nature Chemistry, vol. 3, no. 4, Feb. 2011, pp. 287-290. https://doi.org/10.1038/nchem.1001.