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Synthesis
DOI: 10.1055/a-2503-3181
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Lewis Acid-Catalyzed Regioselective Substitution of 2-Indolylmethanols with Pyrroles

Jun-Nan Gao
1   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China (Ringgold ID: RIN12675)
,
Wen-Xin Tan
1   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China (Ringgold ID: RIN12675)
,
Shuang Yang
1   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China (Ringgold ID: RIN12675)
,
Ning-Yi Wang
1   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China (Ringgold ID: RIN12675)
,
Jiebin Han
2   Department of Otolaryngology, Xuzhou First People’s Hospital, Xuzhou, China
,
Da-Hua Wang
2   Department of Otolaryngology, Xuzhou First People’s Hospital, Xuzhou, China
,
Yu-Chen Zhang 
3   School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, China (Ringgold ID: RIN12675)
,
Feng Shi
1   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, China (Ringgold ID: RIN12675)
› Author AffiliationsSupported by: National Natural Science Foundation of China 22125104 and 22101103
Supported by: Undergraduate Students Project of Jiangsu Province 202110320041Z
Supported by: Science Fund for Distinguished Young Scholars of Jiangsu Province BK20240052
Supported by: Technology Development Fund of the Affiliated Hospital of Xuzhou Medical University XYFY202230
Supported by: Project for Excellent Scientific and Technological Innovation Team of Jiangsu Province
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A Lewis acid-catalyzed regioselective C2’-electrophilic substitution of 2-indolylmethanols with pyrroles was established, which afforded indole-based tetraarylmethanes in overall high yields (up to 99%) with excellent regioselectivities. Moreover, such indole-based tetraarylmethanes exhibited potent cytotoxicity against HepG2 cancer cells, which demonstrated their potential applications in medicinal chemistry. This reaction not only represents the regioselective C2’-electrophilic substitution of 2-indolylmethanols with aryl nucleophiles (Ar-Nu), but also provides a new strategy for the synthesis of biologically important tetraarylmethanes.



Publication History

Received: 25 October 2024

Accepted after revision: 16 December 2024

Accepted Manuscript online:
16 December 2024

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