Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.
J Org Chem, 2012/7/20;77(14):5956-64.
Zhang N[1], Hoffman DJ, Gutsche N, Gupta J, Percec V
Affiliations
PMID: 22712768DOI: 10.1021/jo300547v
Impact factor: 4.198
Abstract
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.
MeSH terms
Benzene Derivatives; Boronic Acids; Catalysis; Mesylates; Molecular Structure; Nickel; Organometallic Compounds; Sulfonic Acids
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