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Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters
Author(s) -
Okita Toshimasa,
Komatsuda Masaaki,
Saito Ami N.,
Hisada Tomoya,
Takahara Tomoaki T.,
Nakayama Keito P.,
Isshiki Ryota,
Takise Ryosuke,
Muto Kei,
Yamaguchi Junichiro
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800207
Subject(s) - dibenzofuran , chemistry , intramolecular force , ligand (biochemistry) , catalysis , palladium , decarbonylation , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , receptor , biochemistry
A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a S N Ar reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron‐rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.