Organic Letters, volume 10, issue 13, pages 2705-2708
Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes
Publication type: Journal Article
Publication date: 2008-06-06
Journal:
Organic Letters
Q1
Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
18533665
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Under the conditions of ruthenium-catalyzed transfer hydrogenation employing 2-propanol as the terminal reductant, 1,1-disubstituted allenes 1a- h engage in reductive coupling to paraformaldehyde to furnish homoallylic alcohols 2a- h. Under identical transfer hydrogenation conditions, 1,1-disubstituted allenes engage in reductive coupling to aldehydes 3a- f to furnish homoallylic alcohols 4a- n. In all cases, reductive coupling occurs with branched regioselectivity to deliver homoallylic alcohols bearing all-carbon quaternary centers.
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Ngai M. Yu., Skucas E., Krische M. J. Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes // Organic Letters. 2008. Vol. 10. No. 13. pp. 2705-2708.
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Ngai M. Yu., Skucas E., Krische M. J. Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes // Organic Letters. 2008. Vol. 10. No. 13. pp. 2705-2708.
Cite this
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TY - JOUR
DO - 10.1021/ol800836v
UR - https://doi.org/10.1021/ol800836v
TI - Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes
T2 - Organic Letters
AU - Ngai, Ming Yu
AU - Skucas, Eduardas
AU - Krische, Michael J
PY - 2008
DA - 2008/06/06
PB - American Chemical Society (ACS)
SP - 2705-2708
IS - 13
VL - 10
PMID - 18533665
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
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@article{2008_Ngai,
author = {Ming Yu Ngai and Eduardas Skucas and Michael J Krische},
title = {Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes},
journal = {Organic Letters},
year = {2008},
volume = {10},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ol800836v},
number = {13},
pages = {2705--2708},
doi = {10.1021/ol800836v}
}
Cite this
MLA
Copy
Ngai, Ming Yu., et al. “Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes.” Organic Letters, vol. 10, no. 13, Jun. 2008, pp. 2705-2708. https://doi.org/10.1021/ol800836v.