Palladium-catalyzed cross-coupling of cyclopropylmagnesium bromide with aryl bromides mediated by zinc halide additives.
The key Pd-catalyzed cross-coupling of aryl bromides or triflates and cyclopropylmagnesium bromide in the presence of substoichiometric amounts of zinc bromide produces cyclopropyl arenes in good to excellent yields. The cross-coupling of other alkyl, cycloalkyl, and aryl Grignard reagents with aryl bromides under the same conditions gives the corresponding substituted arenes in good yields.
Shu
Chutian
C
Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA.
Sidhu
Kanwar
K
Zhang
Li
L
Wang
Xiao-Jun
XJ
Krishnamurthy
Dhileepkumar
D
Senanayake
Chris H
CH
D001965:Bromides / Q000737:chemistry*; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
D001965:Bromides; D006842:Hydrocarbons, Brominated; D009942:Organometallic Compounds; D017967:Zinc Compounds; D047250:Calixarenes; D010165:Palladium; C093802:zinc bromide