Exploring new partners for the domino alfa-arylation/Michael addition reaction leading to tetrahydroisoquinolines

Sulfonates, sulfonamides and phosphonates are useful nucleophiles for palladium-catalyzed intramolecular alfa-arylation leading to tetrahydroisoquinolines. While the sulfonate alfa-arylation can be successfully combined in a domino process with a broad range of Michael acceptors, only vinyl sulfones can be used in Michael additions when starting from sulfonamides. No domino process was developed with the phosphonate derivative. Density functional theory (DFT) calculations were carried out to gain more insight into the experimental differences observed in the reactions involving these substrates.