56366-21-3Relevant academic research and scientific papers
Aromatic C-H coupling with hindered arylboronic acids by Pd/Fe dual catalysts
Yamaguchi, Kazuya,Kondo, Hiroki,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 3753 - 3757 (2013)
An aerobic oxidative coupling of arenes/alkenes with arylboronic acids (C-H/C-B coupling) using catalytic Pd(ii)-sulfoxide-oxazoline (sox) ligand and iron-phthalocyanine (FePc) has been developed. This dual catalyst system enables the synthesis of sterica
Mild and selective base-free C-H arylation of heteroarenes: experiment and computation
Gemoets, Hannes P. L.,Kalvet, Indrek,Nyuchev, Alexander V.,Erdmann, Nico,Hessel, Volker,Schoenebeck, Franziska,No?l, Timothy
, p. 1046 - 1055 (2017/02/10)
A mild and selective C-H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck-Matsuda type coupling mechanism.
