Carbohalogenation Catalyzed by Palladium and Nickel

Abstract

In Chap. 1, a Pd- and Ni-catalyzed cycloisomerization reaction of aryl iodides to alkyl iodides, known as carboiodination, is described. In the Pd-catalyzed variant, a diastereoselective Pd-catalyzed carboiodination reaction of enantioenriched carboxamides generating dihydrosioquinolinones is explored. The transformation was the key step in the formal synthesis of (+)-corynoline. In the Ni-catalyzed variant, 3, 3-disubstituted oxindoles are generated in excellent yield and an enantioselective variant employing a dual ligand system is disclosed.

Parts of this chapter have been reproduced with permission from [Petrone, D. A.; Yoon, H.; Weinstabl, H.; Lautens, M. Angew. Chem. Int. Ed. 2014, 53, 7908.] and [Yoon, H.; Marchese, A. D.; Lautens, M. J. Am. Chem. Soc., 2018, 140, 10950.