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Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline
Verfasser / Verfasserin Gröll, Birgit ; Schaaf, Patricia ; Schnürch, Michael
Erschienen in
Monatshefte für Chemie - Chemical Monthly, Wien, 2017, Jg. 148, H. 1, S. 91-104
ErschienenWien : Springer Vienna, 2017
SpracheEnglisch
DokumenttypAufsatz in einer Zeitschrift
Schlagwörter (EN)Alkynes / Catalysis / Cross dehydrogenative coupling / Oxidative coupling / Copper catalysis
Projekt-/ReportnummerFWF, Project: P21202-N17
ISSN1434-4475
URNurn:nbn:at:at-ubtuw:3-3968 Persistent Identifier (URN)
DOI10.1007/s00706-016-1877-5 
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Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline [0.87 mb]
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Zusammenfassung (Englisch)

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.

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