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Gold‐Photoredox‐Cocatalyzed Tandem Oxycyclization/Coupling Sequence of Allenols and Diazonium Salts with Visible Light Mediation
Author(s) -
Alcaide Benito,
Almendros Pedro,
Aparicio Borja,
LázaroMilla Carlos,
Luna Amparo,
Faza Olalla Nieto
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700598
Subject(s) - chemistry , moiety , tandem , photoredox catalysis , regioselectivity , allene , aryl , photochemistry , combinatorial chemistry , cascade reaction , coupling (piping) , stereochemistry , catalysis , organic chemistry , photocatalysis , materials science , alkyl , composite material , mechanical engineering , engineering
The 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).