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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Nickel-Catalyzed Dehydrogenation-Condensation-Rehydrogenation (DCR) Approach toward the Synthesis of Branched Primary
Adrija Ghosh1, Debasis Banerjee1
1Laboratory of Catalysis and Organic Synthesis, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India.
Abstract:
We demonstrated the first Ni-catalyzed dehydrogenation-condensation-rehydrogenation (DCR) approach for the cross-coupling of two primary alkyl alcohols to β-alkylated primary alcohols. A wide variety of primary alkyl, aryl, and heteroaryl alcohols efficiently coupled with aliphatic primary and secondary alkyl alcohols and released water as a green byproduct (44 entries and up to 96% yield). Straightforward synthesis to chromane and sequential one-pot coupling to C3-substituted quinolines was enabled by nickel catalysis. Initial mechanistic studies including deuterium labeling experiments establish the sequential DCR strategy.
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