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Updated: Feb 21, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Catalytic Reduction of Alkyl and Aryl Bromides Using Propan-2-ol
Michael C Haibach1, Brian M Stoltz1, Robert H Grubbs1
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.
Abstract:
Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of aryl and alkyl halides under relatively mild conditions by using propan-2-ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more functionalized aryl and alkyl bromides. The reduction process is proposed to occur by radical abstraction/hydrodehalogenation steps at ruthenium. Our research represents a safer and more sustainable alternative to typical silane, lithium aluminium hydride, and tin-based conditions for these reductions.
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