Direct Transformations of Amides: Tactics and Recent Progress

doi:10.6023/A18020054

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (5): 357-365.DOI: 10.6023/A18020054 Previous Articles Next Articles

Review

酰胺直接转化:策略与近期进展

黄培强

福建省化学生物学重点实验室能源材料化学协同创新中心厦门大学化学化工学院化学系厦门 361005

投稿日期:2018-02-02 发布日期:2018-03-12
通讯作者: 黄培强,E-mail:pqhuang@xmu.edu.cn E-mail:pqhuang@xmu.edu.cn
作者简介:黄培强,厦门大学教授.1982年毕业于厦门大学化学系,1987获法国南巴黎大学博士学位.中科院上海有机化学研究所博士后. 主要从事有机合成方法学,天然产物全合成,及化学生物学研究.发表论文愈220篇.英国皇家化学会Fellow(2006年). 获原国家教委霍英东青年教师基金(1992年)和国家杰出青年科学基金(1996年).入选新世纪百千万人才工程国家级人选(2006年).先后获得香港"求是"科技基金会"杰出青年学者奖",中国化学会有机化学学科委员会有机合成贡献奖,福建卢嘉锡教育基金会优秀导师奖,2017年教育部自然科学奖二等奖(第一完成人).Eur. J. Org. Chem.,Curr. Org. Synth.,Sci. China-Chem.,Chin. J. Chem.,化学学报,Chin. Chem. Lett.等刊物编委或国际顾问委员会委员.有机化学副主编.
基金资助:
项目受国家重点研发计划（No.2017YFA0207302）、国家自然科学基金（Nos.21332007，21472153，21672176）、教育部长江学者和创新团队发展计划以及中央高校基本科研业务费专项资金（No.20720170092）的资助.

Direct Transformations of Amides: Tactics and Recent Progress

Huang Pei-Qiang

Department of Chemistry, Fujian Provincial Key Laboratory of Chemical Biology, iChEM(Collaborative Innovation Center of Chemistry for Energy Materials), College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China

Received:2018-02-02 Published:2018-03-12
Supported by:
Project supported by the National Key R&D Program of China (grant No. 2017YFA0207302), the National Natural Science Foundation of China (Nos. 21332007, 21472153, 21672176), the Program for Changjiang Scholars and Innovative Research Team in University of the Ministry of Education (P. R. China), and Chinese Universities Scientific Fund (No. 20720170092).

Amides are a class of easily available compounds, and widely serve as versatile intermediates in organic synthesis and medicinal chemistry. Amide-based transformations could lead to many useful compounds and intermediates including various amines, ketones and enaminones. Though direct transformation of amides is of high demand, many current chemoselective transformations are only achieved in multistep approaches. In recent years, direct transformation of amides is emerging as an exciting area. A number of recent progresses on nucleophilic addition to amide carbonyl group that led to new C—C bond formation are highlighted in this review, including (1) in situ amide activation with trifluoromethanesulfonic anhydride (Tf₂O) followed by addition of π- and σ-nucleophiles or reactive organometallic reagents; (2) direct transformation of N-alkoxyamides; (3) direct transformation of amides using Schwartz reagent; and (4) catalytic reductive C—C bond forming reactions of amides, and metal catalyzed coupling of amides.

Key words: amides, functional group transformation, one-pot reactions, synthetic methods, C—C bond formation

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Huang Pei-Qiang. Direct Transformations of Amides: Tactics and Recent Progress[J]. Acta Chim. Sinica, 2018, 76(5): 357-365.

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酰胺直接转化:策略与近期进展

Direct Transformations of Amides: Tactics and Recent Progress

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[2]	Du Chongyang, Chen Yaofeng. ZnEt₂ Promoted Hydrosilylation of CO₂ and Formylation or Urealation of Amines with CO₂ as a C1 Building Block [J]. Acta Chimica Sinica, 2020, 78(9): 938-944.
[3]	Liang Huan, Gou Along, Gao Zhupeng, Lei Linsheng, Wang Bowen, Yu Lan, Xu Xuetao, Wang Shaohua. A New Strategy for the Synthesis of Tertiary Amides via a Copper-Catalyzed Decyanation Reaction of N,N-Disubstituted 2-Aminomalononitriles [J]. Acta Chimica Sinica, 2020, 78(10): 1064-1068.
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[5]	Wang Yuyun, Liu Yunyun. Metal-Free C2-H Aminocarbonylation of Pyridines for the Synthesis of Picolinamides [J]. Acta Chim. Sinica, 2019, 77(5): 418-421.
[6]	Yu Sifan, Fu Xiang, Liu Gengxin, Qiu Huang, Hu Wenhao. Efficient and Facile Synthesis of Chiral Sulfonamides via Asymmetric Multicomponent Reactions [J]. Acta Chim. Sinica, 2018, 76(11): 895-900.
[7]	Huang Lei, Huang Tong, Bai Yongping, Zhou Yongfeng. Hierarchical Self-assembly of Polyamide Helical Fibers [J]. Acta Chim. Sinica, 2016, 74(12): 990-994.
[8]	Jian-Feng Zheng, Zhi-Qiang Xie, Xin-Jian Chen, Pei-Qiang Huang. Direct Transformation of Amides: Reductive Cycloaddition of Secondary Amides with Danishefsky Diene [J]. Acta Chim. Sinica, 2015, 73(7): 705-715.
[9]	Zhan Yizhou, Wang Baolei, Zhang Liyuan, Zhang Yan, Zhang Xiao, Li Zhengming, Song Haibin. Studies on the Synthesis, Structure and Biological Activities of Novel Arylaminoformyl-containing 1-Cyano-1-cycloproane Carboxylic Acid Amides Based on Ugi Reaction [J]. Acta Chim. Sinica, 2015, 73(11): 1173-1181.
[10]	Ma Fei, Chen Jianxin. Novel Method for Synthesis of Unsymmetrical α-Organyl-α-hydroxymalonamide Derivatives [J]. Acta Chimica Sinica, 2013, 71(08): 1118-1120.
[11]	Xiao Kaijiong, Huang Yinghong, Huang Peiqiang. General Direct Transformation of Secondary Amides to Ketones via Amide Activation [J]. Acta Chimica Sinica, 2012, 70(18): 1917-1922.
[12]	Shao Xuebin;Chen Lin;Zhu Shizheng;Li Zhanting;Jiang Xikui. Synthesis of a Porphyrin Derivative Containing Two Quadruple Hydrogen Bonding Moieties [J]. Acta Chimica Sinica, 2003, 61(7): 1040-1046.
[13]	Liu Ping;Zhou Xiaoping;Hu Jianhua;Zhao Qizhong;Deng Wenji;Tong Zhen;Xu Yunhua;Wan Meixiang. Synthesis and Liquid Crystal Properties of a Novel Class of Oligothiophene Derivatives [J]. Acta Chimica Sinica, 2003, 61(5): 774-779.
[14]	Xiao Yuanjing;Wu Xiaojun;Zeng Zhenya;He Yongbing;Meng Lingzhi;Wu Chengtai. Study on Synthesis and Anion Recognition of a Novel Tetraamide Calix [4] (aza) crown [J]. Acta Chimica Sinica, 2003, 61(12): 1986-1990.
[15]	Fang Hao;Xia Lin;Jiang Zhenzhou;Zhang Wei;Zhang Luyong. Design, Synthesis and Biological Activity Study on N-[4- (Substituted Phenyl)piperazine-1-yl]alkyl Amide Series as α_1- Adrenoceptor Antagonists [J]. Acta Chimica Sinica, 2002, 60(4): 725-731.