Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.
Parallel microscale experimentation was used to develop general conditions for the Suzuki-Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. These conditions were found to be amenable to coupling with aryl bromides, iodides, and triflates as well. The conditions that were previously identified through similar techniques to promote the cross-coupling of secondary alkyltrifluoroborates with aryl chlorides were not optimal for the primary alkyltrifluoroborates, thus demonstrating the value of parallel experimentation to develop novel, substrate specific results.
Dreher
Spencer D
SD
Department of Process Research and the Catalytic Reactions Discovery and Development Laboratory, Merck and Co., Inc., Rahway, New Jersey, USA. spencer_dreher@merck.com
Lim
Siang-Ee
SE
Sandrock
Deidre L
DL
Molander
Gary A
GA
D001881:Borates / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008024:Ligands
D001881:Borates; D002712:Chlorides; D007202:Indicators and Reagents; D008024:Ligands