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Journal article
Benzylic C-H activation and C-O bond formation via aryl to benzylic 1,4-palladium migrations
Tetrahedron, Vol.64(26), pp.6090-6102
06/23/2008
Web of Science ID: WOS:000256937700014
Abstract
A procedure for benzylic C-H activation has been developed using a palladium 1,4-aryl to benzylic migration as a key step. Carboxylates and phenoxides readily trap the resulting benzylic palladium intermediates obtained from palladium 'through space' migration. Aryl bromides and iodides have been successfully employed in this reaction, furnishing moderate to good yields. The mechanism of this reaction has been studied by deuterium-labeling experiments, which suggest that the migration of palladium from an aryl to a benzylic position occurs reversibly. The reaction conditions developed for the migration process also oxidize the neighboring benzylic alcohols to the corresponding aldehydes and ketones. (C) 2008 Elsevier Ltd. All rights reserved.
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Details
- Title
- Benzylic C-H activation and C-O bond formation via aryl to benzylic 1,4-palladium migrations
- Publication Details
- Tetrahedron, Vol.64(26), pp.6090-6102
- Resource Type
- Journal article
- Publisher
- Elsevier
- Number of pages
- 13
- Copyright
- Copyright © 2008 Elsevier Ltd. All rights reserved.
- Identifiers
- WOS:000256937700014; 99380482397306600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English