EMAIL THIS PAGE TO A FRIEND

The Journal of organic chemistry

Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes.


PMID 23510098

Abstract

Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins constitute one of the most efficient methods to access them. In this context, oxy- and aminoalkynylation are especially important reactions, because of the numerous transformations possible with the triple bond of acetylenes, yet these methods have been limited to the use of silyl protected acetylenes. Herein, we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes, which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally, a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

373192
Palladium, evaporation slug, diam. × L 0.9 cm × 1.2 cm, 99.95% trace metals basis
Pd
373206
Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis
Pd
348678
Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis
Pd
287474
Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis
Pd
348643
Palladium, foil, thickness 0.25 mm, 99.98% trace metals basis
Pd
411450
Palladium, foil, thickness 0.05 mm, 99.9% trace metals basis
Pd
267120
Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis
Pd
203998
Palladium, granular, 99.99% trace metals basis
Pd
203939
Palladium, powder, 99.999% trace metals basis
Pd
464651
Palladium, powder, <75 μm, 99.9% trace metals basis
Pd
326666
Palladium, powder, <1 μm, ≥99.9% trace metals basis
Pd
346985
Palladium, rod, diam. 6.25 mm, ≥99.9% trace metals basis
Pd
267082
Palladium, sponge, 99.9% trace metals basis
Pd
267112
Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis
Pd
348694
Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis
Pd
643181
Palladium, extent of labeling: 5 wt. % loading (dry basis), matrix activated carbon, wet support, Degussa type E105CA/W
Pd
686468
Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%
Pd
520810
Palladium black, surface area 40-60 m2/g, 99.95% trace metals basis
Pd