1310708-89-4Relevant articles and documents
Base-promoted SNAR reactions of fluoro- And chloroarenes as a route to N-aryl indoles and carbazoles
Iqbal, Muhammad Asif,Mehmood, Hina,Lv, Jiaying,Hua, Ruimao
, (2019)
KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.
Rhodium (III)-catalyzed regioselective direct C-2 alkenylation of indoles assisted by the removable N-(2-pyrimidyl) group
Gong, Binwei,Shi, Jingjing,Wang, Xiaowei,Yan, Yunnan,Li, Qiu,Meng, Yanqiu,Xu, H. Eric,Yi, Wei
, p. 137 - 143 (2014)
The C-2-alkenylindole unit is a key component of numerous natural products and pharmacophores. However, the intermolecular direct construction of the core structural motif remains challenging in organic synthesis. Here we report a new, efficient, and versatile methodology for the synthesis of C-2-alkenylindoles through rhodium (III)-catalyzed direct C-H functionalization of indoles with acrylates under air by employing a metal-directing group strategy. This strategy gives a rare selectivity for the alkenylation N-(2-pyrimidyl)indoles at the C-2 position and provides the functionalized C-2- alkenylindoles under mild conditions with broad substrate tolerance. An expansion of the methodology has also been demonstrated to, for example, the direct alkenylation of pyrrole and facile deprotection of the pyrimidyl group. All the results suggest that this methodology could be served as a highly attractive alternative for the direct construction of biologically important C-2-alkenylindoles.
Rhodium-Catalyzed Additive-Free C?H Ethoxycarbonylation of (Hetero)Arenes with Diethyl Dicarbonate as a CO Surrogate
Kawai, Yuya,Liao, Yumeng,Matsuda, Takanori,Suzuki, Hirotsugu
supporting information, p. 4938 - 4942 (2021/09/30)
A rhodium-catalyzed C(sp2)-H ethoxycarbonylation of indoles and arylpyridines using diethyl dicarbonate was developed. The catalytic process features an additive-free ethoxycarbonylation reaction, in which only ethanol and CO2 are produced as byproducts, providing a CO-free and operationally simple protocol. The introduced ethoxycarbonyl group is easily transformed into other ester and amide functionalities in a single step. Moreover, the reaction can be successfully applied on gram scale, and allows for the efficient synthesis of indole-2-carboxylic acid esters and isophthalates.
The copper(ii)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles
Zhang, Dong,Fang, Zheng,Cai, Jinlin,Liu, Chengkou,He, Wei,Duan, Jindian,Qin, Ning,Yang, Zhao,Guo, Kai
supporting information, p. 8119 - 8122 (2020/08/03)
A novel and efficient approach for the highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(ii) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive molecules containing an indole ring was achieved in good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and excellent C-2 selectivity. This journal is
