Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 41, Issue 4, Pages 1582-1590Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202101003
Keywords
umpolung; dearomatization; indole-2-methanols; 3,3 '-bisindoles
Categories
Funding
- National Natural Science Foundation of China [21602087]
- Top-notch Academic Programs Project of Jiangsu Higher Education Institutions
- National College Student.s Innovation and Entrepreneurship Training Program [201910320093Z]
Ask authors/readers for more resources
A new Sc(OTf)(3)-catalyzed dearomatization of indole-2-methanols has been reported, providing a series of 3,3'-bisindoles with exocyclic double bond unit in moderate to excellent yields. The importance of the N-sulfonyl group in the dearomatization process was highlighted in the study.
A new Sc(OTf)(3)-catalyzed dearomatization of indole-2-methanols is reported. By using the characteristics of umpolung of the preformed indole-2-methanols in the presence of acid catalysts, its nucleophilic center at 3-position of indole ring could be transformed into the electrophilic site, thereby realizing the coupling reaction with another molecule indoles, which led to the synthesis of a series of 3,3'-bisindoles with exocyclic double bond unit in moderate to excellent yields. Among them, the strong induction and large steric effects of N-sulfonyl group are the key to the dearomatization of indole ring from indole-2-methanols. Based on the experimental results and literature reports, the possible reaction mechanism is proposed, which involves the dehydroxylation and nucleophilic addition of indole-2-methanol derivatives. In addition, this protocol features high functional group compatibility, mild conditions and simple operation.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available