Synthesis and reactivity of mixed alkynylalanes by direct triethylamine-catalyzed alumination of terminal alkynes.

Christophe Feuvrie (1) , Jérôme Blanchet (2) , Martine Bonin (3) , Laurent Micouin (3)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCMT - Laboratoire de chimie moléculaire et thioorganique
3 SSMIP - Synthèse et structure de molécules d'interet pharmacologique

[reaction: see text] Terminal alumination of alkynes by DIBALH or trimethylaluminum can be performed in a simple manner in the presence of a small amount of triethylamine. This new Lewis-base-catalyzed process delivers mixed alkynyldialkylalanes of great interest, without the need of an initial deprotonation step with lithium or sodium derivatives followed by a transmetalation.

Domaines: Chimie organique

Christophe Feuvrie, Jérôme Blanchet, Martine Bonin, Laurent Micouin. Synthesis and reactivity of mixed alkynylalanes by direct triethylamine-catalyzed alumination of terminal alkynes.. Organic Letters, 2004, 6 (14), pp.2333-6. ⟨10.1021/ol049346v⟩. ⟨hal-00909871⟩