Citation: ZHU Yuelu, ZHAO Xinyang, WU Qian, CHEN Ying, ZHAO Jing. Research Advances in C―H Bond Activation of Multitasking N-Phenoxyamides[J]. Acta Physico-Chimica Sinica, ;2019, 35(9): 989-1004. doi: 10.3866/PKU.WHXB201812016 shu

Research Advances in C―H Bond Activation of Multitasking N-Phenoxyamides

ZHU Yuelu ¹ ,
ZHAO Xinyang ¹ ,
WU Qian ² ,
CHEN Ying ² ,
ZHAO Jing ^1,,

1.
State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China
2.
Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, Guangdong Province, P. R. China

Corresponding author: ZHAO Jing, jingzhao@nju.edu.cn
Received Date: 5 December 2018
Revised Date: 15 January 2019
Accepted Date: 15 January 2019
Available Online: 21 September 2019
Fund Project: The project was supported by the National Science Foundation of China (21622103, 21571098, 91753121), Natural Science Foundation of Jiangsu Province, China (BK20160022), Shenzhen Basic Research Program, China (JCYJ20170413150538897), and Fundamental Research Funds for the Central Universities, China (020514380139)the National Science Foundation of China 21571098the National Science Foundation of China 91753121Fundamental Research Funds for the Central Universities, China 020514380139Natural Science Foundation of Jiangsu Province, China BK20160022the National Science Foundation of China 21622103Shenzhen Basic Research Program, China JCYJ20170413150538897

Transition-metal-catalyzed C―H functionalization reactions, assisted by directing groups (DGs), have become some of the most powerful strategies to form C―C and C―X (X = O, N, S, etc.) bonds. It has brought about a revolution in the synthesis of drugs and natural products, and the method is widely applicable in the fields of material chemistry and pharmaceutical industry. This strategy has mainly focused on regioselective C―H functionalization of amides, esters, carbamates, and enamides with DGs to form C―C and C―X bonds. Since these DGs are relatively stable, they must be removed by other methods when the reaction is completed. Therefore, the use of a traceless DG is one of the important challenges for transition-metal-catalyzed C―H functionalization. Recently, N-phenoxyamide has been attracting significant research attention as a versatile DG. Oxyacetamide (O―NHAc) is one of the most versatile functionalities for directed C―H functionalization cascades, such as the internal oxidation with N―O bond cleavage. The O―NHAc has been reported as a superb DG for redox-neutral C―H activation/annulation cascade reactions to synthesize phenol and complex heterocyclic scaffolds by coupling with alkynes, alkenes, heteroarenes, and diazo compounds. However, for the external oxidation with preservation of the N―O bond, e.g. when a stoichiometric external oxidant is present, N-phenoxyamides could react with aldehydes or α, β-unsaturated aldehydes. In addition, the solvent can control the chemoselectivity. In this minireview, the C―H bond functionalization of N-phenoxyamide is divided into five categories according to the different substrates, viz. alkenes, alkynes, diazo, and other compounds and intramolecular C―H bond activation reactions. Based on experimental and theoretical research results, the reaction mechanism was discussed. In the first part, we summarize the ortho-alkylation, alkenylation, and cyclization of N-phenoxyamide with olefins. In the second part, we present the Rh- and Ir-catalyzed C―H activation or cyclization of N-phenoxyamide with alkanes to synthesize phenol or benzofuran compounds. In the third part, we describe the synthesis of phenolic compounds functionalized by Rh-catalyzed diazo compounds by carbene intermediates and N-phenoxyamides. The forth part summarizes the C―H activation/annulation reaction using aldehydes, heterocyclic aromatic, and sulfur reagents as substrates. The last part of the paper generalizes the intramolecular ortho-hydroxylation and ortho, para-amidation reactions.
- C―H activation,
- N-phenoxyamides,
- Multitasking,
- Phenols,
- Selenium
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沈阳化工大学材料科学与工程学院沈阳 110142