Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.
The efficiency of arylboron-based nucleophiles, boronic acid, potassium trifluoroborate, neopentylglycolboronate, and pinacol boronate in nickel-catalyzed Suzuki-Miyaura cross-coupling reactions with the two C-O electrophiles, mesylates, and sulfamates was compared. Arylboronic acid is the most reactive and most atom-economic of the four boron species studied. Arylpotassium trifluoroborate cross-couples efficiently only in the presence of water. In the absence of water, aryl neopentylglycolboronate is more efficient, less expensive, and more atom-economic than aryl pinacolboronate.
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Na
N
Zhang
David J
DJ
Hoffman
Nicholas
N
Gutsche
Jayesh
J
Gupta
Virgil
V
Percec
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*
D001555:Benzene Derivatives; D001897:Boronic Acids; D008698:Mesylates; D009942:Organometallic Compounds; D013451:Sulfonic Acids; D009532:Nickel; C005741:sulfamic acid