Aromatic homolytic substitution using solid phase synthesis

Steven M. Allin; W. Russell Bowman; Rehana Karim; Shahzad S. Rahman

doi:10.1016/j.tet.2006.02.071

Aromatic homolytic substitution using solid phase synthesis

Steven M. Allin, W. Russell Bowman, Rehana Karim, Shahzad S. Rahman

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

Abstract

Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.

Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors.

Original language	English
Pages (from-to)	4306-4316
Journal	Tetrahedron Letters
Volume	62
Issue number	18
DOIs	https://doi.org/10.1016/j.tet.2006.02.071
Publication status	Published - 1 May 2006

Keywords

Aryl radicals
Radical cyclisation
solid-phase synthesis
Microwave
Benzoimidazoles

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10.1016/j.tet.2006.02.071

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title = "Aromatic homolytic substitution using solid phase synthesis",

abstract = "Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors.",

keywords = "Aryl radicals, Radical cyclisation, solid-phase synthesis, Microwave, Benzoimidazoles",

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T1 - Aromatic homolytic substitution using solid phase synthesis

AU - Allin, Steven M.

AU - Bowman, W. Russell

AU - Karim, Rehana

AU - Rahman, Shahzad S.

PY - 2006/5/1

Y1 - 2006/5/1

N2 - Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors.

AB - Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors.

KW - Aryl radicals

KW - Radical cyclisation

KW - solid-phase synthesis

KW - Microwave

KW - Benzoimidazoles

U2 - 10.1016/j.tet.2006.02.071

DO - 10.1016/j.tet.2006.02.071

M3 - Article

SN - 0040-4039

VL - 62

SP - 4306

EP - 4316

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Aromatic homolytic substitution using solid phase synthesis

Abstract

Keywords

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