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Re‐Catalyzed Annulations of Weakly Coordinating N ‐Carbamoyl Indoles/Indolines with Alkynes via C−H/C−N Bond Cleavage
Author(s) -
Yang Yunhui,
Wang Congyang
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901518
Subject(s) - rhenium , catalysis , chemistry , cleavage (geology) , bond cleavage , medicinal chemistry , ring (chemistry) , combinatorial chemistry , stereochemistry , organic chemistry , materials science , fracture (geology) , composite material
Described herein are rhenium‐catalyzed [3+2] annulations of N ‐carbamoyl indoles with alkynes via C−H/C−N bond cleavage, which provide rapid access to fused‐ring pyrroloindolone derivatives. For the first time, the weakly coordinating O‐directing group was successfully employed in rhenium‐catalyzed C−H activation reactions, enabled by the unique catalytic trio of Re 2 (CO) 10 , Me 2 Zn and ZnCl 2 . Mechanistic studies revealed that aminozinc species plays an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic trio of Re 2 (CO) 10 , [MeZnNPh 2 ] 2 and Zn(OTf) 2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivatives.