The Benzoyl Peroxide Promoted Dual C–C Bond Formation via Dual C–H Bond Cleavage: α-Phenanthridinylation of Ether by Isocyanide
Organic Letters2014Vol. 16(8), pp. 2088–2091
Citations Over TimeTop 1% of 2014 papers
Abstract
The benzoyl peroxide-promoted α-phenanthridinylation of ether by isocyanide is developed, proceeding through dual C-H bond cleavage and dual C-C bond formation. The procedure tolerates a series of functional groups, such as methyl, fluoro, chloro, acetyl, methoxy carbonyl, cyano, and trifluoromethyl. Thus, it represents a facile pathway leading to 6-substituted phenanthridine derivatives. The addition of radical to the isonitrile followed by a radical aromatic cyclization is involved in this transformation.
Related Papers
- → Electrochemical cyclization of 1-phenyl-2(-1′chlorophenyl)-substituted five-membered nitrogen heterocycles. Application to the synthesis of phenanthridines(1990)24 cited
- → Conformational Studies of (±)‐11,12‐Didehydro‐11‐deoxycorynoline and (+)‐11,13‐Didehydro‐11‐deoxychelidonine, Hexahydrobenzo[c]phenanthridine‐Type Alkaloid Derivatives, by X‐Ray Crystal Structure and NMR Analyses(2010)6 cited
- → Studies on Phenanthridine Derivatives. IV(1951)1 cited
- → Morgan‐Walls Cyclization(2010)1 cited