Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization.
A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates. [reaction: see text]
Giri
Ramesh
R
Department of Chemistry MS015, Brandeis University, Waltham, MA 02454-9110, USA.
Wasa
Masayuki
M
Breazzano
Steven P
SP
Yu
Jin-Quan
JQ
D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D013696:Temperature
D003521:Cyclopropanes; D007202:Indicators and Reagents; D010165:Palladium