Advanced Synthesis and Catalysis, volume 352, issue 14-15, pages 2416-2420
Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.
Publication type: Journal Article
Publication date: 2010-09-23
Journal:
Advanced Synthesis and Catalysis
Q1
Q1
SJR: 1.020
CiteScore: 9.4
Impact factor: 4.4
ISSN: 16154150, 16154169
PubMed ID:
21165157
Abstract
Exposure of alcohols 1a-1i to butadiene in the presence of a cyclometallated iridium catalyzed derived from allyl acetate, 4-methoxy-3-nitrobenzoic acid and BIPHEP (2,2'-bis(diphenylphosphino)biphenyl) results in hydrogen transfer to generate aldehyde-allyliridium pairs, which engage in C-C coupling to form products of carbonyl crotylation. Under related conditions using 1,4-butanediol as hydrogen donor, butadiene reductively couples to aldehydes 2e-2g and 2i to furnish carbonyl crotylation products 3e-3g and 3i. Thus, butadiene mediated carbonyl crotylation occurs with equal facility from the alcohol or aldehyde oxidation level with complete levels of branched regioselectivity.
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Zbieg J. R., Fukuzumi T., Krische M. J. Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation. // Advanced Synthesis and Catalysis. 2010. Vol. 352. No. 14-15. pp. 2416-2420.
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Zbieg J. R., Fukuzumi T., Krische M. J. Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation. // Advanced Synthesis and Catalysis. 2010. Vol. 352. No. 14-15. pp. 2416-2420.
Cite this
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TY - JOUR
DO - 10.1002/adsc.201000599
UR - https://doi.org/10.1002/adsc.201000599
TI - Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.
T2 - Advanced Synthesis and Catalysis
AU - Zbieg, Jason R
AU - Fukuzumi, Takeo
AU - Krische, Michael J.
PY - 2010
DA - 2010/09/23
PB - Wiley
SP - 2416-2420
IS - 14-15
VL - 352
PMID - 21165157
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
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@article{2010_Zbieg,
author = {Jason R Zbieg and Takeo Fukuzumi and Michael J. Krische},
title = {Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.},
journal = {Advanced Synthesis and Catalysis},
year = {2010},
volume = {352},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/adsc.201000599},
number = {14-15},
pages = {2416--2420},
doi = {10.1002/adsc.201000599}
}
Cite this
MLA
Copy
Zbieg, Jason R., et al. “Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation..” Advanced Synthesis and Catalysis, vol. 352, no. 14-15, Sep. 2010, pp. 2416-2420. https://doi.org/10.1002/adsc.201000599.