Noncryogenic I/Br−Mg Exchange of Aromatic Halides Bearing Sensitive Functional Groups Using i-PrMgCl−Bis[2-(N,N-dimethylamino)ethyl] Ether Complexes
Organic Letters2005Vol. 8(2), pp. 305–307
Citations Over TimeTop 12% of 2005 papers
Abstract
[reaction: see text] Iodo- and bromoaromatics bearing sensitive carboxylic ester and cyano groups underwent a selective halide-magnesium exchange with isopropylmagnesium chloride at ambient temperature in the presence of bis[2-(N,N-dimethylamino)ethyl] ether to afford the corresponding Grignard reagents. The newly formed reactive Grignard reagents were allowed to react with electrophiles such as trimethylborate to afford arylboronic acids in good to excellent yields.
Related Papers
- → Shift Happens. How Halide Ion Defects Influence Photoinduced Segregation in Mixed Halide Perovskites(2017)358 cited
- → How Lead Halide Complex Chemistry Dictates the Composition of Mixed Halide Perovskites(2016)242 cited
- → 4.07 Electrophilic Cyclization(2014)16 cited
- → Isomeric exocyclic and endocyclic dienolates: behavior towards electrophiles(1985)7 cited
- → Interconversion of Halides(2018)