Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles

Erik Tullberg; F Schacher; D Peters; Torbjörn Frejd

doi:10.1055/s-2006-926371

Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles

Erik Tullberg, F Schacher, D Peters, Torbjörn Frejd

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1183-1189
Journal	Synthesis
Issue number	7
DOIs	https://doi.org/10.1055/s-2006-926371
Publication status	Published - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Free keywords

palladium
Heck reaction
green chemistry
cyclizations
indoles

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10.1055/s-2006-926371

Cite this

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title = "Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles",

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.",

keywords = "palladium, Heck reaction, green chemistry, cyclizations, indoles",

author = "Erik Tullberg and F Schacher and D Peters and Torbj{\"o}rn Frejd",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

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doi = "10.1055/s-2006-926371",

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T1 - Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles

AU - Tullberg, Erik

AU - Schacher, F

AU - Peters, D

AU - Frejd, Torbjörn

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2006

Y1 - 2006

N2 - 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.

AB - 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.

KW - palladium

KW - Heck reaction

KW - green chemistry

KW - cyclizations

KW - indoles

U2 - 10.1055/s-2006-926371

DO - 10.1055/s-2006-926371

M3 - Article

SN - 0039-7881

SP - 1183

EP - 1189

JO - Synthesis

JF - Synthesis

IS - 7

ER -

Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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