Ortho-C-H Benzylation of Aryl Imines with Benzyl Phosphates under Cobalt-Pyphos Catalysis

Organic Letters
Wengang XuNaohiko Yoshikai

Abstract

Ortho-C-H benzylation of aryl ketimines with benzyl phosphates is achieved with the aid of a catalytic system consisting of a cobalt(II) salt, a phosphine/pyridine bidentate ligand, and a Grignard reagent under room-temperature conditions, affording a variety of diarylmethanes bearing o-acetyl or -acyl groups in moderate to good yields. Owing to the versatility of the o-acetyl group, the reaction opens useful synthetic routes to polycyclic compounds such as unsymmetrical anthracene, anthracenone, and anthraquinone derivatives.

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Citations

Jul 20, 2017·Organic Letters·Bo LiBing-Feng Shi
Sep 1, 2018·Chemistry : a European Journal·Martin Pichette DrapeauMarc Taillefer
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen
Oct 1, 2019·Chemical Communications : Chem Comm·Shuguang XieZhong Jin

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