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Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system.
J Org Chem. 2013 Apr 05; 78(7):3030-8.JO

Abstract

A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Huang L
Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Institute of Applied Chemistry, Shaoxing University, Shaoxing, Zhejiang Province 312000, People's Republic of China.
Li Q
No affiliation info available
Wang C
No affiliation info available
Qi C
No affiliation info available

MeSH

1-NaphthylamineAminoquinolinesCatalysisHydrocarbons, IodinatedModels, MolecularMolecular ConformationNaphthalenesOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23425227

Citation

Huang, Lehao, et al. "Palladium(II)-catalyzed Regioselective Arylation of Naphthylamides With Aryl Iodides Utilizing a Quinolinamide Bidentate System." The Journal of Organic Chemistry, vol. 78, no. 7, 2013, pp. 3030-8.
Huang L, Li Q, Wang C, et al. Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system. J Org Chem. 2013;78(7):3030-8.
Huang, L., Li, Q., Wang, C., & Qi, C. (2013). Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system. The Journal of Organic Chemistry, 78(7), 3030-8. https://doi.org/10.1021/jo400017v
Huang L, et al. Palladium(II)-catalyzed Regioselective Arylation of Naphthylamides With Aryl Iodides Utilizing a Quinolinamide Bidentate System. J Org Chem. 2013 Apr 5;78(7):3030-8. PubMed PMID: 23425227.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system. AU - Huang,Lehao, AU - Li,Qian, AU - Wang,Chen, AU - Qi,Chenze, Y1 - 2013/02/20/ PY - 2013/2/22/entrez PY - 2013/2/22/pubmed PY - 2013/10/1/medline SP - 3030 EP - 8 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 7 N2 - A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23425227/Palladium_II__catalyzed_regioselective_arylation_of_naphthylamides_with_aryl_iodides_utilizing_a_quinolinamide_bidentate_system_ L2 - https://doi.org/10.1021/jo400017v DB - PRIME DP - Unbound Medicine ER -