Abstract
We report an efficient protocol for tandem Pd-catalyzed intramolecular addition of active methylene compounds to alkynes, followed by subsequent cross-coupling with (hetero)aryl bromides and chlorides. The reaction proceeds under mild conditions, providing excellent functional group tolerance, including unprotected OH, NH2 groups, enolizable ketones, or a variety of heterocycles. Mechanistic studies point towards a catalytic cycle involving oxidative addition, intramolecular nucleophilic addition to the Pd(ii)-activated alkyne, and reductive elimination, with 5-exo-dig cyclization being the rate limiting step.
Highlights
Palladium complexes emerge as some of the most versatile homogenous catalysts with a myriad of applications in both academic and industrial research
The ability to mediate mechanistically distinct transformations makes palladium the catalyst of choice for the design of tandem reactions in which a single metal complex catalyzes a sequence of transformations.[2]
We are focused on the development of tandem processes combining the nucleophilic addition to alkynes and subsequent cross-coupling, which give the access to a wide set of carbo- and heterocyclic systems.[3]
Summary
Palladium complexes emerge as some of the most versatile homogenous catalysts with a myriad of applications in both academic and industrial research.
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