Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C−O Bond Formation under Mild Conditions

A method for the synthesis of dihydrobenzofurans by a direct aryl C−O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-09, Vol.55 (38), p.11625-11628
Main Authors: Alvarado, Joseph, Fournier, Jeremy, Zakarian, Armen
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzofurans - chemical synthesis
Benzofurans - chemistry
Bonding
Carbon - chemistry
Catalysis
Coordination Complexes - chemistry
copper
Copper - chemistry
Cyclization
fused-ring systems
iodonium salts
Oxygen - chemistry
oxygen heterocycles
Stereoisomerism
Substrates
Synthesis
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Summary:A method for the synthesis of dihydrobenzofurans by a direct aryl C−O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates. Take a walk on the mild side: A method for the synthesis of dihydrobenzofurans minimizing competitive alcohol oxidation is described. The mild reaction conditions are compatible with functional groups not used previously in such transformations. A key step in this process is the in situ formation of an iodonium salt.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201605648