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Catalytic Reduction of Alkyl and Aryl Bromides Using Propan‐2‐ol

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.

Einfach komplex: Der Milstein‐Komplex (PNN)RuHCl(CO) katalysiert die effiziente Reduktion von Alkylbromiden und ‐chloriden durch Propan‐2‐ol unter Verwendung einer Base. Sterisch gehinderte tertiäre und Neopentylsubstrate werden ebenso umgesetzt wie funktionalisierte Aryl‐ und Alkylbromide. Die vermutlich radikalische Reaktion bildet eine Alternative zu Reduktionen mit Silanen, Lithiumaluminiumhydrid und Zinnreagentien.

Authors:   Michael C. Haibach, Brian M. Stoltz, Robert H. Grubbs; Michael C. Haibach, Brian M. Stoltz, Robert H. Grubbs
Journal:   Angewandte Chemie
Volume:   129
edition:   47
Year:   2017
Pages:   15319
DOI:   10.1002/ange.201708800
Publication date:   24-Oct-2017
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