The Mechanism of Bu3SnH-Mediated Homolytic Aromatic Substitution

Athelstan L.J. Beckwith; Vincent W. Bowry; W. Russell Bowman; Emma Mann; Jonathan Parr; John M.D. Storey

doi:10.1002/anie.200352419

The Mechanism of Bu₃SnH-Mediated Homolytic Aromatic Substitution

Athelstan L.J. Beckwith^*, Vincent W. Bowry, W. Russell Bowman, Emma Mann, Jonathan Parr, John M.D. Storey

^*Corresponding author for this work

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

121 Citations (Scopus)

Abstract

The fate of intermediate π radicals is crucial in Bu ₃SnH-mediated cyclization by homolytic aromatic substitution, for example, of bromo compound 1 via radical 2 to give oxindole 3 (AIBN = azobisisobutyronitrile). The results indicate that the mechanism requires the abstraction of a hydrogen radical from the intermediate π radical by the radical initiator or a product of initiator breakdown, and also that arene solvents are not always the best solvents for radical reactions.

Original language	English
Pages (from-to)	95-98
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	1
DOIs	https://doi.org/10.1002/anie.200352419
Publication status	Published - 22 Dec 2004

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abstract = "The fate of intermediate π radicals is crucial in Bu 3SnH-mediated cyclization by homolytic aromatic substitution, for example, of bromo compound 1 via radical 2 to give oxindole 3 (AIBN = azobisisobutyronitrile). The results indicate that the mechanism requires the abstraction of a hydrogen radical from the intermediate π radical by the radical initiator or a product of initiator breakdown, and also that arene solvents are not always the best solvents for radical reactions.",

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AU - Storey, John M.D.

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AB - The fate of intermediate π radicals is crucial in Bu 3SnH-mediated cyclization by homolytic aromatic substitution, for example, of bromo compound 1 via radical 2 to give oxindole 3 (AIBN = azobisisobutyronitrile). The results indicate that the mechanism requires the abstraction of a hydrogen radical from the intermediate π radical by the radical initiator or a product of initiator breakdown, and also that arene solvents are not always the best solvents for radical reactions.

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KW - Cyclization

KW - Radical reactions

KW - Radicals

KW - Reaction mechanisms

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The Mechanism of Bu₃SnH-Mediated Homolytic Aromatic Substitution

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