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Rhodium(III)‐Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C−H Bond Activation
Author(s) -
Meng YanYu,
Zhu WenJing,
Song YuanYuan,
Bu GangGang,
Zhang LiJuan,
Xu Fen
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001634
Subject(s) - chemistry , annulation , rhodium , alkyne , catalysis , moiety , bond cleavage , cleavage (geology) , stereochemistry , medicinal chemistry , selectivity , combinatorial chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
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.