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- Title
Rhodium(III)‐Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C−H Bond Activation.
- Authors
Meng, Yan‐Yu; Zhu, Wen‐Jing; Song, Yuan‐Yuan; Bu, Gang‐Gang; Zhang, Li‐Juan; Xu, Fen
- Abstract
In this paper, a rhodium‐catalyzed sequential two‐fold ortho‐C−H functionalization of N‐phenylbenzimidamide with internal alkyne is reported. The double C−H activations proved viable in a one‐pot fashion with the assistance of C=N and C−N bonds, providing a series of benzimidazoisoquinolines with high levels of positional selectivity control. The operationally simple transformation showed high functional group compatibility and featured the cleavage of C−H bonds located on different a moiety of the N‐phenylbenzimidamide substrates. Detailed mechanistic studies provided strong support for C−H bond cleavage on the N‐phenyl ring to be preferential compared with C−H bond cleavage on C‐phenyl ring. As a multifunctional catalytic platform, the rhodium catalyst conducted two independent and compatible catalytic cycles in one pot.
- Subjects
RHODIUM catalysts; RHODIUM; SCISSION (Chemistry); AMIDINES; ANNULATION; ALKYNES; CLASS B metals
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 8, p1290
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202001634