Pd-catalyzed C-H arylation of N-sulfonyl indole derivatives

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Pd-catalyzed C-H arylation of N-sulfonyl indole derivatives
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                        Tan JingTan Jing
College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University
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Sun MeijiaoSun Meijiao
College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University
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Wu WenqianWu Wenqian
College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University
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Peng JinsongPeng Jinsong
College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University
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Chen ChunxiaChen Chunxia
College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University
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Affiliation:College of Chemistry,Chemical Engineering and Resource Utilization,Northeast Forestry University
Clc Number:TQ426；O641.4
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Abstract:

Using iodoarenes as arylation reagents, Pd-catalyzed sulfonyl group-directed selectively C-Harylation of indoles was investigated in detail. The results showed N-tosyl indole can be converted into 2- and 7-arylated products with an overall yield of 93% in 1, 4-dioxaneat 120 ℃for 24 h with Pd(OAc)2/PPh3 as the catalyst, Na2CO3 as the base and Ag2CO3 as the additive. Under these optimized conditions, the scope and limitation of the synthetic method were examined by using different aryl iodides to obtain 28 indole-based compounds in 22%~93% total yields, and the structure of corresponding indole products were elucidated by 1H NMR, 13C NMR and HRMS spectra.

Key words:palladium catalysis; indole framework; C-H functionalization; arylation; directing group

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Received:April 13,2023
Revised:June 06,2023
Adopted:June 06,2023
Online: January 09,2024
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