N-Halosuccinimide enables cascade oxidative trifluorination and halogenative cyclization of tryptamine-derived isocyanides

Jun-Yunzi Wu, Long-Ling Huang, Jia-Luo Fu, Jia-Yi Li, Shuang Lin, Shuang Yang, Zhi-Shu Huang, Honggen Wang () and Qingjiang Li ()
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Jun-Yunzi Wu: Sun Yat-sen University
Long-Ling Huang: Sun Yat-sen University
Jia-Luo Fu: Sun Yat-sen University
Jia-Yi Li: Sun Yat-sen University
Shuang Lin: Sun Yat-sen University
Shuang Yang: Sun Yat-sen University
Zhi-Shu Huang: Sun Yat-sen University
Honggen Wang: Sun Yat-sen University
Qingjiang Li: Sun Yat-sen University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Both the pyrroloindoline core and N–CF3 moiety hold significant importance in medicinal chemistry. However, to date, no instances of constructing N–CF3-containing pyrroloindolines have been reported. Herein, we present a robust and operationally simple approach to assembling such intriguing skeletons from tryptamine-derived isocyanides through a cascade sequence, which includes an oxidative trifluorination and a subsequent halogenative cyclization. Key to the success lies in the development of a facile conversion of isocyanides to N–CF3 moiety with commercially available reagents N-halosuccinimide and Et3N·HF. The protocol features mild reaction conditions, broad functional group tolerance, good to excellent yields, and high diastereoselectivities. In addition, we demonstrate that the halide substituent within the products serves as a versatile functional handle for accessing diverse C3-quaternary-substituted N–CF3-pyrroloindolines.

Date: 2024
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DOI: 10.1038/s41467-024-53271-9

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