Journal
ORGANIC LETTERS
Volume 16, Issue 16, Pages 4308-4311Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol502023d
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Funding
- National Science Foundation [CHE-1058855]
- KU Center for Environmentally Beneficial Catalysis
- Kansas Bioscience Authority Rising star program
- NSF-MRI [CHE-0923449]
- NSF Academic Research Infrastructure Grant [9512331]
- NIH Shared Instrumentation Grant [S10RR024664]
- NSF Major Research Instrumentation Grant [0320648]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1058855] Funding Source: National Science Foundation
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The direct coupling of allyl alcohols with nitroalkanes, nitriles, and aldehydes using catalytic Pd(PPh3)(4) has been accomplished via activation of C-OH bonds with CO2. The in situ formation of carbonates from alcohols and CO2 facilitates oxidative addition to Pd to form reactive pi-allylpalladium intermediates. In addition, the formation of a strong base activates nucleophiles toward the reaction with the pi-allylpalladium electrophile. Overall, this atom economical reaction provides a new C-C bond without the use of an external base and generates water as the only byproduct.
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