Palladium(0)-Catalyzed Synthesis of Indoles and Carbazoles from o- Alkenyl (Alkyl) Anilines via C-H Amination Cyclization

Various indoles and carbazoles were synthesized from o-alkenyl anilines and o-aryl anilines by the beta-C(sp(2))-H bond amination cyclization without any oxidants or hydrogen acceptors. Likewise, employing o-alkyl anilines as substrates, indole products are also obtained by the beta-C(sp(3))-H bond...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 13; no. 9
Main Authors Zhao, Yinglin, Yang, Xuesu, Zhu, Yifei, Yuan, Yuqin, Wang, Ruitong, Liu, Renhua
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.09.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
2-ALKENYLANILINES
FUNCTIONALIZATION
beta-C(sp)-H bond amination cyclization
Without any oxidants
Dehydrogenation
UNUSUAL 1,2-ARYL MIGRATION
REGIOSELECTIVE SYNTHESIS
C(SP)-H AMINATION
ALKENYLANILIDES
3,1-BENZOXAZINES
Waste-free
METAL-FREE
ALKALOIDS
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Summary:Various indoles and carbazoles were synthesized from o-alkenyl anilines and o-aryl anilines by the beta-C(sp(2))-H bond amination cyclization without any oxidants or hydrogen acceptors. Likewise, employing o-alkyl anilines as substrates, indole products are also obtained by the beta-C(sp(3))-H bond amination cyclization, and dehydrogenation. In this cross-dehydrogenative coupling, many different functional groups are tolerated, and hydrogen gas is the only by-product, thereby providing an intrinsically waste-free approach for the synthesis of indoles and carbazoles.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202400268