Palladium and Nickel Catalyzed Transformations Forming Functionalized Heterocycles (eBook)

This book presents Pd- and Ni-catalyzed transformations generating functionalized heterocycles. Transition metal catalysis is at the forefront of synthetic organic chemistry since it offers new and powerful methods to forge carbon-carbon bonds in high atom- and step-economy.

In Chapter 1, the author describes a Pd- and Ni-catalyzed cycloisomerization of aryl iodides to alkyl iodides, known as carboiodination. In the context of the Pd-catalyzed variant, the chapter explores the production of enantioenriched carboxamides through diastereoselective Pd-catalyzed carboiodination. It then discusses Ni-catalyzed reactions to generate oxindoles and an enantioselective variant employing a dual ligand system.

Chapter 2 introduces readers to a Pd-catalyzed diastereoselective anion-capture cascade. It also examines diastereoselective Pd-catalyzed aryl cyanation to synthesize alkyl nitriles, a method that generates high yields of borylated chromans as a single diastereomer, and highlights its synthetic utility.  

Lastly, Chapter 3 presents a Pd-catalyzed domino process harnessing carbopalladation, C-H activation and ?-system insertion (benzynes and alkynes) to generate spirocycles. It also describes the mechanistic studies performed on these reactions.

Hyung Yoon received his B.Sc. from the University of Toronto in 2013, and in 2018 he completed his Ph.D. at the University of Toronto under the supervision of Professor Mark Lautens, primarily focusing on developing new methods in palladium and nickel catalyzed transformations. During his Ph.D., he also undertook research in the Glorius group at the University of Münster as a member of the Integrated Research Training Group (IRTG). He is currently an NSERC postdoctoral fellow in the Miller group, where he is investigating late-stage functionalization using transition metals.