Cycloaddition reactions using immobilized alkynes. A proof of concept for an integral use of the outcoming products in solid-phase synthetic methodologies

RIVEIRA, M. J.; MATA, E. G.; DIEZ, C. M.; MISCHNE, M. P.

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Año: 2018 p. 10001 - 10014

0022-3263

The transition-metal-catalyzed [2+2+2]-cycloaddition of alkynes has become a powerful atom-economical strategy for aromatic ring construction. Unfortunately, the control of the stereo-, regio- and chemoselectivity of these processes is usually challenging and these reactions can potentially lead to complex unuseful mixtures. While solid-phase chemistry has proven to be a successful tool for decreasing the number of cycloadducts formed and for facilitating the purification step, an integral use of the outcoming products in this complex reaction is described herein. By using an immobilized monoalkyne, the transition-metal-catalyzed [2+2+2]-cycloaddition with soluble 1,6-diyne-esters led to the clean and simultaneous preparation of soluble and solid-supported phthalides, showing a new way to benefit from solid-phase synthetic methodologies.