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Gold-Photoredox-Cocatalyzed Tandem Oxycyclization/Coupling Sequence of Allenols and Diazonium Salts with Visible Light Mediation

AuthorsAlcaide, Benito ; Almendros, Pedro ; Aparicio, Borja; Lázaro-Milla, Carlos; Luna, Amparo; Nieto, Olalla
Density functional calculations
Synthetic methods
Issue Date2017
PublisherJohn Wiley & Sons
CitationAdvanced Synthesis and Catalysis 359: 2789-2800 (2017)
AbstractThe room temperature radical cycloetherification/arylation cascade of allenols and diazonium salts has been accomplished via a combination of gold and photoredox catalysis to provide 2,3,4-trisubstituted-2,5-dihydrofurans. The functionalized oxacycle formation sequence is chemo- and regioselective for the cycloetherification and for the position that bears the aryl moiety after the cross-coupling. Mechanistic investigations revealed that this transformation proceeds through an initial oxidation of gold(I) to a phenyl gold(III) complex, which, upon coordination to the allene, catalyzes its cyclization and leads to the coupling product after a reductive elimination regenerating Au(I). (Figure presented.).
Publisher version (URL)http://dx.doi.org/10.1002/adsc.201700598
Identifiersdoi: 10.1002/adsc.201700598
issn: 1615-4150
e-issn: 1615-4169
Appears in Collections:(IQOG) Artículos
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