Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline

Alkynylation reactions of N-protected tetrahydroisoquinolines have been performed using several different protocols of cross dehydrogenative coupling. Initially, a CuCl-catalyzed method was investigated, which worked well with three different N-protecting groups, namely phenyl, PMP, and benzyl and t-BuOOH as oxidant in acetonitrile as solvent. The peroxide could then be replaced by simple air and acetonitrile for water, leading to an overall very environmentally friendly protocol. Finally, a decarboxylative alkynylation protocol starting from alkynoic acids was also developed using again air as oxidant. This avoids the use of gaseous alkynes in the introduction of short-chained alkyne substituents.Austrian Science Foundation (FWF)911041

Multi-objective optimization for clustering 3-way gene expression data

Multi-objective optimization, Clustering, Fuzzy C-means, Microarray, Gene expression data, 62-07,