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

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Styrene
Cobalt
Derivatives
Catalysts
Photosensitizing Agents
Photosensitizers
Vitamin B 12
Functional groups
Temperature
Experiments
tris(2,2'-bipyridyl)ruthenium(II)
Organic Chemistry
cobaloxime

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Visible Light-Driven, Room Temperature Heck-Type Reaction of Alkyl Halides with Styrene Derivatives Catalyzed by B12 Complex",
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.).",
author = "Li Chen and Yoshio Hisaeda and Hisashi Shimakoshi",
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AU - Chen, Li

AU - Hisaeda, Yoshio

AU - Shimakoshi, Hisashi

PY - 2019/6/18

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N2 - 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.).

AB - 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.).

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