Zn(II)-Stabilized Azo-Anion Radical-Catalyzed Dehydrogenative Synthesis of Olefins

Herein, we describe a Zn-catalyzed atom-economical, inexpensive, and sustainable method for preparing a broad spectrum of substituted olefins utilizing alcohols as the main precursor. Using a Zn­(II) complex [ZnLCl2] (1) of the redox-noninnocent ligand 2-((4-chlorophenyl)­diazenyl)-1,10-phenanthroli...

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Veröffentlicht in:Journal of organic chemistry 2024-12, Vol.90 (1), p.225-239
Hauptverfasser: Pal, Subhasree, Guin, Amit Kumar, Khanra, Subhankar, Paul, Nanda D.
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we describe a Zn-catalyzed atom-economical, inexpensive, and sustainable method for preparing a broad spectrum of substituted olefins utilizing alcohols as the main precursor. Using a Zn­(II) complex [ZnLCl2] (1) of the redox-noninnocent ligand 2-((4-chlorophenyl)­diazenyl)-1,10-phenanthroline (L), various (E)-olefins were prepared in good yields by coupling alcohols with sulfones and aryl cyanides under an inert atmosphere. Under an aerial atmosphere, vinyl nitriles were isolated in up to 82% yield reacting alcohols with benzyl cyanides in the presence of 1. Control experiments and mechanistic investigation indicate the active involvement of the aryl-azo ligand as an electron and hydrogen reservoir, permitting 1 to perform as a promising catalyst.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02158