Fe(III)-Based Tandem Catalysis for Amidomethylative Multiple Substitution Reactions of alpha-Substituted Styrene Derivatives

Developing tandem multiple C-H substitution reactions of simple alkenes provides rapid access to structurally complex unsaturated building blocks. Amidomethylative reactions that reserve C=C double bonds have been composed sequentially for tandem catalytic substitutions around the C=C bonds of alkenes. As a proof-of-concept demonstration, tandem catalytic amidomethylative processes, which effectively form multiple C-C bonds, have been developed to directly and selectively transform a-substituted styrenes into unsaturated N-heterocycles. Using Fe(OTf)(3) as the sole catalyst, the operationally simple protocols employ bench-stable bisamidomethane as the sole reagent to produce hexahydropyrimidines and 1,2,3,6-tetrahydropyridine derivatives. Moreover, the practical catalytic processes constituted facile two-step pathways, from simple alpha-substituted styrenes, to access unsaturated 1,3-diamine and bispidine derivatives.