期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 3, 页码 2840-2853出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02782
关键词
-
资金
- National Natural Science Foundation of China [21908094]
A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes through a palladium-catalyzed perfluoroalkyl insertion reaction has been developed. This method utilized multiple iodofluoroalkanes as practical perfluoroalkyl sources, providing a simple and versatile route for the synthesis of perfluoroalkylated indoles. Furthermore, it was also applied to late-stage C2 perfluoroalkylation of bioactive compounds such as auxin, tryptophan, and melatonin analogues.
A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes through a palladium-catalyzed perfluoroalkyl insertion reaction has been accomplished. This protocol employed multiple iodofluoroalkanes as practical and available perfluoroalkyl sources to provide an operationally simple and versatile route for the synthesis of perfluoroalkylated indoles. Moreover, indoles without the assistance of guide groups were utilized as substrates, achieving C(sp(2))-H site-selective functionalization of indoles in yields up to 95%. Furthermore, this protocol was also used for late-stage C2 perfluoroalkylation of bioactive compounds such as auxin, tryptophan, and melatonin analogues.
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