Rhodium (II) acetate and Nafion-H catalyzed decomposition of N-aryldiazoamides. Efficient synthesis of 2 (3H)-indolinones

…, MS Shanklin, HQ Pho, SN Mahapatro

Index: Doyle, Michael P.; Shanklin, Michael S.; Pho, Hoan Q.; Mahapatro, Surendra N. Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1017 - 1022

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Citation Number: 104

Abstract

N-Aryldiazoamides undergo facile intramolecular aromatic substitution to form 2 (3H)- indolinones in high yield when these reactions are performed in the presence of a catalytic amount of rhodium (I1) acetate. Diazoacetamides react smoothly at room temperature in dichloromethane, whereas the corresponding less reactive diazoacetoacetamides respond in refluxing benzene. A meta methoxy substituent directs substitution solely to its para ...