Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 14, Pages 5956-5964Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300547v
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Funding
- NSF [DMR-1066116, DMS-0935165]
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1066116] Funding Source: National Science Foundation
- Division Of Mathematical Sciences
- Direct For Mathematical & Physical Scien [0935165] Funding Source: National Science Foundation
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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. la the absence of water, aryl neopentylglycolboronate is more efficient, less expensive, and more atom-economic than aryl pinacolboronate.
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