Regioselective Preparation of 2-Phenylethylamines from 1-Phenyl-2-alkylalkynes
by Hydroamination/Reduction Sequences
Andreas Heutling, René Severin, Sven Doye*
SYNTHESIS 2004, No. x, pp 000A–000Ex.x.204
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Abstract: Ind2TiMe2 is a highly active and general catalyst for the intermolecular hydroamination of alkynes. Particularly impressive is that Ind2TiMe2 makes it possible to perform hydroamination reactions of unsymmetrically substituted 1-phenyl-2-alkylalkynes with primary aryl-, tert-alkyl-, sec-alkyl-, and n-alkylamines in a highly regioselective fashion. Since the initially formed imines can easily be reduced with zinc-modified NaBH3CN, 2-phenylethylamines are accessible in reliable one-pot procedures from 1-phenyl-2-alkylalkynes and primary amines on a 10 mmol scale.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000537159-amination_schematic.jpg)