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Highly Flexible Synthesis of 2‐Arylethylamine Derivatives
Author(s) -
Siebeneicher Holger,
Doye Sven
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:7<1213::aid-ejoc1213>3.0.co;2-g
Subject(s) - alkyne , hydroamination , chemistry , sonogashira coupling , aryl , combinatorial chemistry , alkyl , halide , coupling reaction , regioselectivity , palladium , catalysis , organic chemistry
A new and highly flexible procedure for the synthesis of 2‐arylethylamine derivatives is described. By the new procedure, the target compounds can be synthesized with high diversity in three steps from aryl halides, terminal alkynes, and primary amines. The reaction sequence starts with a palladium‐catalyzed coupling of an aryl halide and a terminal alkyne (Sonogashira coupling). A subsequent Cp 2 TiMe 2 ‐catalyzed hydroamination of the obtained alkyl(aryl)alkyne, which takes place regioselectively in the 2‐position, gives access to an α‐arylketimine. A final reduction with NaBH 3 CN/ZnCl 2 ·Et 2 O results in the formation of the desired 2‐arylethylamine derivative. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)