Transition Metal-free α-C-H Functionalization of Tertiary Amines Catalysed/Promoted by Acids: A Brief Review

被引:0
作者
Deb, Mohit L. [1 ]
Baruah, Pranjal K. [1 ]
机构
[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India
关键词
C-H functionalization; acid catalyst; transition metal-free; tert-amine; N-heterocycle; H-shift; CATALYZED OXIDATIVE CYANATION; ACTIVATION; BONDS; CONSTRUCTION; REDUCTION; EFFICIENT; AMIDES;
D O I
10.2174/1570193X20666230309091635
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H Functionalization of alpha-carbon of tertiary amines has been of great importance for the past two decades as N-heterocycles can be synthesized by this approach and these heterocycles are highly useful as drugs or drug precursors in the pharmaceutical industry. In this review article, we have summarized only the alpha-C-H functionalization reactions of tertiary amines that are catalysed or promoted by acids. These C-H functionalization reactions are usually catalysed by transition metal salts, although metal-free catalysts are also used. However, several such reactions have been reported that are efficiently catalysed by acids. They are cost-effective, have a simple purification process, less sensitive to air/moisture, and are relatively environmentally benign. However, this area has not received enough focus due to the lack of review articles, which encouraged us to write this review.
引用
收藏
页码:445 / 454
页数:10
相关论文
共 50 条
[31]   Metal-free and site-selective α-C-H functionalization of tetrahydrofuran enabled by the photocatalytic generation of bromine radicals [J].
Zhu, Can-Ming ;
Liang, Rong-Bin ;
Xiao, Yonghong ;
Zhou, Wei ;
Tong, Qing-Xiao ;
Zhong, Jian-Ji .
GREEN CHEMISTRY, 2023, 25 (03) :960-965
[32]   Regioselective Transition-Metal-Catalyzed C-H Functionalization of Anilines [J].
Leitch, Jamie A. ;
Frost, Christopher G. .
SYNTHESIS-STUTTGART, 2018, 50 (14) :2693-2706
[33]   Recent advancements in metal-free C-C bond formation via C-H bond functionalization [J].
Sikder, Ankita ;
Sengupta, Jhimli .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (11) :2539-2571
[34]   Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand [J].
Chen, Yixuan ;
Gu, Yuefei ;
Meng, Huan ;
Shao, Qianzhen ;
Xu, Zhenchuang ;
Bao, Wenjing ;
Gu, Yucheng ;
Xue, Xiao-Song ;
Zhao, Yanchuan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (28)
[35]   Transition Metal-Free Direct C-H Functionalization of Quinones and Naphthoquinones with Diaryliodonium Salts: Synthesis of Aryl Naphthoquinones as β-Secretase Inhibitors [J].
Wang, Dawei ;
Ge, Bingyang ;
Li, Liang ;
Shan, Jie ;
Ding, Yuqiang .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18) :8607-8613
[36]   Metal-free visible light mediated direct C-H amination of benzoxazole with secondary amines [J].
Beg, Mohd. Zaheeruddin ;
Singh, Pravin K. ;
Singh, Praveen P. ;
Srivastava, Manish ;
Srivastava, Vishal .
MOLECULAR DIVERSITY, 2024, 28 (01) :61-71
[37]   Metal-free C-H Borylation and Hydroboration of Indoles [J].
Nad, Pinaki ;
Mukherjee, Arup .
ACS OMEGA, 2023, 8 (41) :37623-37640
[38]   Metal-free catalytic C-H bond activation and borylation of heteroarenes [J].
Legare, Marc-Andre ;
Courtemanche, Marc-Andre ;
Rochette, Etienne ;
Fontaine, Frederic-Georges .
SCIENCE, 2015, 349 (6247) :513-516
[39]   Transition-metal-catalyzed C-H functionalization of pyrazoles [J].
Kang, Eunsu ;
Kim, Hyun Tae ;
Joo, Jung Min .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (32) :6192-6210
[40]   Recent Advances in C-H Functionalization Using Electrochemical Transition Metal Catalysis [J].
Ma, Cong ;
Fang, Ping ;
Mei, Tian-Sheng .
ACS CATALYSIS, 2018, 8 (08) :7179-7189