An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.
An amine-N-oxide-ligated n class="Chemical">palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.
Authors: Kyle Clagg; Haiyun Hou; Adam B Weinstein; David Russell; Shannon S Stahl; Stefan G Koenig Journal: Org Lett Date: 2016-07-12 Impact factor: 6.005
Authors: H M D Bandara; D Jin; M A Mantell; K D Field; A Wang; R P Narayanan; N A Deskins; M H Emmert Journal: Catal Sci Technol Date: 2016-03-24 Impact factor: 6.119
Authors: Kumiko Yamamoto; Jiakun Li; Jeffrey A O Garber; Julian D Rolfes; Gregory B Boursalian; Jannik C Borghs; Christophe Genicot; Jérôme Jacq; Maurice van Gastel; Frank Neese; Tobias Ritter Journal: Nature Date: 2018-02-21 Impact factor: 49.962