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Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides.
Org Lett. 2020 Jul 17; 22(14):5517-5521.OL

Abstract

A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.

Authors+Show Affiliations

Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chemicals, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32602725

Citation

Li, Zhaohui, et al. "Palladium-Catalyzed N-Acylation of Tertiary Amines By Carboxylic Acids: a Method for the Synthesis of Amides." Organic Letters, vol. 22, no. 14, 2020, pp. 5517-5521.
Li Z, Liu L, Xu K, et al. Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides. Org Lett. 2020;22(14):5517-5521.
Li, Z., Liu, L., Xu, K., Huang, T., Li, X., Song, B., & Chen, T. (2020). Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides. Organic Letters, 22(14), 5517-5521. https://doi.org/10.1021/acs.orglett.0c01869
Li Z, et al. Palladium-Catalyzed N-Acylation of Tertiary Amines By Carboxylic Acids: a Method for the Synthesis of Amides. Org Lett. 2020 Jul 17;22(14):5517-5521. PubMed PMID: 32602725.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides. AU - Li,Zhaohui, AU - Liu,Long, AU - Xu,Kaiqiang, AU - Huang,Tianzeng, AU - Li,Xinyi, AU - Song,Bin, AU - Chen,Tieqiao, Y1 - 2020/06/30/ PY - 2020/7/1/pubmed PY - 2020/7/1/medline PY - 2020/7/1/entrez SP - 5517 EP - 5521 JF - Organic letters JO - Org. Lett. VL - 22 IS - 14 N2 - A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/32602725/Palladium-Catalyzed_N-Acylation_of_Tertiary_Amines_by_Carboxylic_Acids:_A_Method_for_the_Synthesis_of_Amides L2 - https://doi.org/10.1021/acs.orglett.0c01869 DB - PRIME DP - Unbound Medicine ER -
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