volume 51 issue 31 pages 7830-7834

Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides

Publication typeJournal Article
Publication date2012-06-26
scimago Q1
wos Q1
SJR5.550
CiteScore27.6
Impact factor16.9
ISSN14337851, 15213773
General Chemistry
Catalysis
Abstract
It takes alkynes! Exposure of propargyl chlorides to primary benzylic alcohols in the presence of [Ir(cod){(R)-segphos}]OTf (cod = 1,5-cyclooctadiene, segphos = 5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole, Tf = trifluoromethanesulfonyl) results in hydrogen exchange to give allenyliridium-aldehyde pairs that combine to form products of propargylation with high ee value (see scheme). The reaction can also be conducted using aldehydes.
Found 
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Woo S. K., Geary L. M., Krische M. J. Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides // Angewandte Chemie - International Edition. 2012. Vol. 51. No. 31. pp. 7830-7834.
GOST all authors (up to 50) Copy
Woo S. K., Geary L. M., Krische M. J. Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides // Angewandte Chemie - International Edition. 2012. Vol. 51. No. 31. pp. 7830-7834.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/anie.201203334
UR - https://doi.org/10.1002/anie.201203334
TI - Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides
T2 - Angewandte Chemie - International Edition
AU - Woo, Sang Kook
AU - Geary, Laina M.
AU - Krische, Michael J
PY - 2012
DA - 2012/06/26
PB - Wiley
SP - 7830-7834
IS - 31
VL - 51
PMID - 22736416
SN - 1433-7851
SN - 1521-3773
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Woo,
author = {Sang Kook Woo and Laina M. Geary and Michael J Krische},
title = {Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides},
journal = {Angewandte Chemie - International Edition},
year = {2012},
volume = {51},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/anie.201203334},
number = {31},
pages = {7830--7834},
doi = {10.1002/anie.201203334}
}
MLA
Cite this
MLA Copy
Woo, Sang Kook, et al. “Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides.” Angewandte Chemie - International Edition, vol. 51, no. 31, Jun. 2012, pp. 7830-7834. https://doi.org/10.1002/anie.201203334.