Palladium — Catalyzed Reactions, 1 Palladium‐Catalyzed Enantioselective Hydrophenylation and Hydrohetarylation of Bicyclo[2.2.1]Hept‐2‐ene: Influence of the Chiral Ligand, the Leaving Group, and the Solvent

Abstract

Abstract The use of optically active biaryl bisphosphanes 10 – 12 , a diphenylphosphanylphenyloxazoline 8 , and a (β‐N‐sulfonyl‐aminomethyl)bisdiphenylphosphane 7 as ligands in the Pd‐catalyzed Heck‐type hydroarylation of norbornene ( 1 ) with phenyl 2 and various hetaryl derivaties 3 – 5 leads exclusively to the formation of exo‐2(het)arylnorbornanes 6 with asymmetric inductions of up to 86.4% ee. In addition to an investigation into the effects of different chiral ligands, a systematic study has been made of the influence of various (het)aryl compounds, leaving groups, and solvents on the chemical and optical yields of this reductive arylation.