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Palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides leading to alkyl aryl ketones.
Org Lett. 2011 May 06; 13(9):2184-7.OL

Abstract

A new, simple method for selectively synthesizing alkyl aryl ketones has been developed by palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides. In the presence of PdCl(2)(MeCN)(2), TBAB, and ZnO, a variety of aryl iodides underwent an oxidative coupling reaction with tertiary amines and water to afford the corresponding alkyl aryl ketones in moderate to excellent yields. It is noteworthy that this method is the first example of using trialkylamines as the carbonyl sources for constructing alkyl aryl ketone skeletons.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu Y
College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325035, China.
Yao B
No affiliation info available
Deng CL
No affiliation info available
Tang RY
No affiliation info available
Zhang XG
No affiliation info available
Li JH
No affiliation info available

MeSH

AlkylationAminesCatalysisIodidesKetonesMolecular StructureOxidation-ReductionPalladium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21473627

Citation

Liu, Yan, et al. "Palladium-catalyzed Oxidative Coupling of Trialkylamines With Aryl Iodides Leading to Alkyl Aryl Ketones." Organic Letters, vol. 13, no. 9, 2011, pp. 2184-7.
Liu Y, Yao B, Deng CL, et al. Palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides leading to alkyl aryl ketones. Org Lett. 2011;13(9):2184-7.
Liu, Y., Yao, B., Deng, C. L., Tang, R. Y., Zhang, X. G., & Li, J. H. (2011). Palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides leading to alkyl aryl ketones. Organic Letters, 13(9), 2184-7. https://doi.org/10.1021/ol200404z
Liu Y, et al. Palladium-catalyzed Oxidative Coupling of Trialkylamines With Aryl Iodides Leading to Alkyl Aryl Ketones. Org Lett. 2011 May 6;13(9):2184-7. PubMed PMID: 21473627.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides leading to alkyl aryl ketones. AU - Liu,Yan, AU - Yao,Bo, AU - Deng,Chen-Liang, AU - Tang,Ri-Yuan, AU - Zhang,Xing-Guo, AU - Li,Jin-Heng, Y1 - 2011/04/07/ PY - 2011/4/9/entrez PY - 2011/4/9/pubmed PY - 2011/7/30/medline SP - 2184 EP - 7 JF - Organic letters JO - Org Lett VL - 13 IS - 9 N2 - A new, simple method for selectively synthesizing alkyl aryl ketones has been developed by palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides. In the presence of PdCl(2)(MeCN)(2), TBAB, and ZnO, a variety of aryl iodides underwent an oxidative coupling reaction with tertiary amines and water to afford the corresponding alkyl aryl ketones in moderate to excellent yields. It is noteworthy that this method is the first example of using trialkylamines as the carbonyl sources for constructing alkyl aryl ketone skeletons. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21473627/Palladium_catalyzed_oxidative_coupling_of_trialkylamines_with_aryl_iodides_leading_to_alkyl_aryl_ketones_ L2 - https://doi.org/10.1021/ol200404z DB - PRIME DP - Unbound Medicine ER -