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Rh(III)‐Catalyzed Redox‐Neutral Cascade Annulation of Benzamides with p ‐Quinone Methides
Author(s) -
Kanchupalli Vinaykumar,
Shukla Rahul K.,
Singh Anurag,
Volla Chandra M. R.
Publication year - 2020
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.202000863
Subject(s) - chemistry , annulation , quinone methide , redox , quinone , intramolecular force , cascade reaction , alkyne , catalysis , conjugate , tandem , stereochemistry , combinatorial chemistry , cascade , sequence (biology) , medicinal chemistry , organic chemistry , mathematical analysis , biochemistry , materials science , mathematics , composite material , chromatography
Herein, we demonstrate a [RhCp*Cl 2 ] 2 catalyzed synthesis of isoindolo[2,1‐ b ]isoquinolin‐5( 7H )‐one derivatives from N ‐(pivaloyloxy)benzamides and p ‐quinone methides under redox neutral conditions. p ‐Quinone methide derivatives were engaged for the first time as precursors in C–H activation reactions and the cascade sequence consists of Rh(III)‐catalyzed C–H activation, alkyne insertion followed by an intramolecular 1,6‐conjugate addition. This novel tandem reaction strategy offers a rapid and straightforward access to complex fused isoquinolinone derivatives in an efficient manner.