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- Title
Rhodium-Catalyzed Regioselective Synthesis of Isoindolium Salts from 2-Arylpyridines and Alkenes in Aqueous Medium under Oxygen.
- Authors
Upadhyay, Nitinkumar Satyadev; Jayakumar, Jayachandran; Cheng, Chien ‐ Hong
- Abstract
A highly regioselective synthesis of pyrido[2,1- a]isoindolium salts from 2-arylpyridines and two equivalents of electron-deficient alkenes catalyzed by rhodium is demonstrated. The reaction was carried out in aqueous medium at 110 °C using inexpensive oxygen as oxidant. Reverse aza-Michael addition of the isoindolium salt occurs when the salt was treated with base to give a β-disubstituted alkene product. A reaction mechanism involving an ortho C-H olefination of 2-arylpyridine by alkene, intramolecular aza-Michael addition, deprotonation at the β-carbon of the alkene fragment followed by another Michael addition to give the final product is proposed.
- Subjects
RHODIUM catalysts; REGIOSELECTIVITY (Chemistry); ALKENES; MICHAEL reaction; REACTION mechanisms (Chemistry)
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 21, p3381
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600452