Visible Light-Driven, Room Temperature Heck-Type Reaction of Alkyl Halides with Styrene Derivatives Catalyzed by B12 Complex

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Abstract

A visible light driven Heck-type coupling reaction of alkyl halides with styrene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ru(bpy)3]Cl2 photosensitizer at room temperature is reported. The catalytic efficiencies of the B12 catalyst were compared to that of other cobalt complexes such as cobaloxime. Various control experiments supported a radical-based mechanism similar to those for typical B12 model reactions. A unique coupling reaction combined with 1,2-migration of the functional group is also reported. Mild reaction conditions using an environmentally benign cobalt catalyst derived from the natural B12 provided a practical protocol for the synthetic organic chemistry of the B12 catalyzed reaction system. (Figure presented.).

Original languageEnglish
Pages (from-to)2877-2884
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number12
DOIs
Publication statusPublished - Jun 18 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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