Solvent-Free Heck-Jeffery Reactions under Ball-Milling Conditions Applied to the Synthesis of Unnatural Amino Acids Precursors and Indoles

Erik Tullberg; Felix Schacher; Dan Peters; Torbjörn Frejd

doi:10.1055/s-2006-926371

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Synthesis 2006(7): 1183-1189
DOI: 10.1055/s-2006-926371

PAPER

Solvent-Free Heck-Jeffery Reactions under Ball-Milling Conditions Applied to the Synthesis of Unnatural Amino Acids Precursors and Indoles

Erik Tullberg^a, Felix Schacher^b, Dan Peters^c, Torbjörn Frejd*^a
^a Department of Organic Chemistry 1, Lund University, P. O. Box 124, 22100 Lund, Sweden
Fax: +46(46)2224119; e-Mail: Torbjorn.Frejd@organic.lu.se;
^b Makromolecular Chemistry II, Naturwissenschaften II (NW II), 95440 Bayreuth, Germany
^c NeuroSearch A/S, Pederstrupvej 93, 2750 Ballerup, Denmark

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Publication History

Received 29 September 2005
Publication Date:
08 March 2006 (online)

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Abstract

The syntheses of various amino- and hydroxy-substituted dehydrophenylalanine derivatives using the Heck-Jeffery protocol under non-solvent conditions in a ball mill are presented. The influences of electron-withdrawing groups and of the location of the heteroatom substituent relative to the halide are discussed. Suitably substituted ortho-amino dehydrophenylalanine derivatives undergo a cyclization-elimination reaction to the corresponding 2-substituted indoles.

Key words

cyclizations - indoles - green chemistry - Heck reaction - palladium

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