Rh-catalyzed regioselective ortho-C-H carbenoid insertion of diarylazines

Yunliang Yu (1) , Changsheng Kuai (1) , Rémi Chauvin (2, 3) , Nian Tian (1) , Shuangshuang Ma (1) , Xiuling Cui (1)

1 Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University
2 LCC - Laboratoire de chimie de coordination
3 UT3 - Université Toulouse III - Paul Sabatier

The Rh-catalyzed ortho-C–H carbenoid insertion reaction of diarylazines with diazo compounds has been developed. A wide range of ortho-substituted diarylazines have been obtained in moderate to high yields with high regioselectivity at room temperature. The hydrolysis of the products could release ketones or aldehydes, giving access to aromatic 1,5-keto-diesters as valuable synthons for further chemical transformations.

Mots clés: Additives; Hydrocarbons; Addition reactions; Aromatic compounds; Solvents

Domaines: Chimie de coordination

Yunliang Yu, Changsheng Kuai, Rémi Chauvin, Nian Tian, Shuangshuang Ma, et al.. Rh-catalyzed regioselective ortho-C-H carbenoid insertion of diarylazines. Journal of Organic Chemistry, 2017, 82 (16), pp.8611-8616. ⟨10.1021/acs.joc.7b01472⟩. ⟨hal-01939395⟩