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Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group.
J Org Chem. 2021 05 21; 86(10):7296-7303.JO

Abstract

The direct arylation of aliphatic ketones has been developed via Pd-catalyzed β-C(sp3)-H bond functionalization with 2-(aminooxy)-N,N-dimethylacetamide as a novel transient directing group (TDG), which showed remarkable directing ability to generate arylated products in moderate to good yields. Furthermore, the reaction can tolerate abundant substrate of ketones and aryl iodides. This study expands the scope of applications for TDGs.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang Y
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P.R. China.
Wu G
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P.R. China.
Xu X
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P.R. China.
Pang B
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P.R. China.
Liao S
Shanghai Jinli Pharmaceutical Co. Ltd., 108 Yuegong Road, Shanghai 201507, P.R. China.
Ji Y
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P.R. China.

MeSH

CatalysisIodidesKetonesPalladium

Pub Type(s)

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

Language

eng

PubMed ID

33950672

Citation

Wang, Yangyang, et al. "Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled By a Transient Directing Group." The Journal of Organic Chemistry, vol. 86, no. 10, 2021, pp. 7296-7303.
Wang Y, Wu G, Xu X, et al. Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group. J Org Chem. 2021;86(10):7296-7303.
Wang, Y., Wu, G., Xu, X., Pang, B., Liao, S., & Ji, Y. (2021). Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group. The Journal of Organic Chemistry, 86(10), 7296-7303. https://doi.org/10.1021/acs.joc.1c00646
Wang Y, et al. Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled By a Transient Directing Group. J Org Chem. 2021 05 21;86(10):7296-7303. PubMed PMID: 33950672.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group. AU - Wang,Yangyang, AU - Wu,Gaorong, AU - Xu,Xiaobo, AU - Pang,Binghan, AU - Liao,Shaowen, AU - Ji,Yafei, Y1 - 2021/05/05/ PY - 2021/5/6/pubmed PY - 2021/7/8/medline PY - 2021/5/5/entrez SP - 7296 EP - 7303 JF - The Journal of organic chemistry JO - J Org Chem VL - 86 IS - 10 N2 - The direct arylation of aliphatic ketones has been developed via Pd-catalyzed β-C(sp3)-H bond functionalization with 2-(aminooxy)-N,N-dimethylacetamide as a novel transient directing group (TDG), which showed remarkable directing ability to generate arylated products in moderate to good yields. Furthermore, the reaction can tolerate abundant substrate of ketones and aryl iodides. This study expands the scope of applications for TDGs. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/33950672/Palladium_Catalyzed_β_C_sp3__H_Arylation_of_Aliphatic_Ketones_Enabled_by_a_Transient_Directing_Group_ DB - PRIME DP - Unbound Medicine ER -