Exploring Partners for the Domino α‐Arylation/Michael Addition Reaction Leading to Tetrahydroisoquinolines

Abstract

Sulfonates, sulfonamides, and phosphonates have proven useful nucleophiles for palladium‐catalyzed intramolecular α‐arylation reactions leading to tetrahydroisoquinolines. Although the sulfonate α‐arylation reaction 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. DFT calculations were carried out to gain more insights into the experimental differences observed in the reactions involving these substrates.

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

“…The preference of one mechanism or the other is strongly determined by the electrophilicity of the Michael acceptor. 70 Interestingly, the Mizoroki−Heck reaction never occurred under these reaction conditions.…”

Site Selectivity in Pd-Catalyzed Reactions of α-Diazo-α-(methoxycarbonyl)acetamides: Effects of Catalysts and Substrate Substitution in the Synthesis of Oxindoles and β-Lactams

“…As part of our research program on the synthesis of nitrogen heterocycles, we have been exploring different ways to increase the versatility of palladium catalysis in C–C bond-forming reactions [49,50,51], for example, by controlling the ambiphilic character of the organopalladium intermediates in the intramolecular coupling reactions with carbonyl derivatives [52]. Continuing our search for methodologies to enhance the synthetic potential of organopalladium chemistry, we have also investigated the versatility of palladium as a catalyst for the carbene C–H insertion.…”