Remote nucleophilic allylation by allylrhodium chain walking

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Groves, Alistair, Martinez, Jose I., Smith, Joshua J. and Lam, Hon Wai (2018) Remote nucleophilic allylation by allylrhodium chain walking. Chemistry - A European Journal . ISSN 0947-6539

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Abstract

Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and an imine to give Z-homoallylic alcohols and amines, respectively.

Item Type: Article
RIS ID: https://nottingham-repository.worktribe.com/output/946308
Additional Information: This is the peer reviewed version of the following article, which has been published in final form at https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201803574. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Keywords: allylation, chain walking, homogenous catalysis, isomerization, rhodium
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1002/chem.201803574
Depositing User: Smith, Ruth
Date Deposited: 20 Jul 2018 10:04
Last Modified: 04 May 2020 19:46
URI: https://eprints.nottingham.ac.uk/id/eprint/53051

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