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Remote Nucleophilic Allylation by Allylrhodium Chain Walking

Martínez, Jose I.; Groves, Alistair; Martinez, Jose I.; Smith, Joshua J.; Lam, Hon Wai

Authors

Jose I. Martínez

Jose I. Martinez

Joshua J. Smith

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



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.

Citation

Martínez, J. I., Groves, A., Martinez, J. I., Smith, J. J., & Lam, H. W. (2018). Remote Nucleophilic Allylation by Allylrhodium Chain Walking. Chemistry - A European Journal, 24(51), 13432-13436. https://doi.org/10.1002/chem.201803574

Journal Article Type Article
Acceptance Date Jul 13, 2018
Online Publication Date Jul 13, 2018
Publication Date Sep 12, 2018
Deposit Date Jul 20, 2018
Publicly Available Date Jul 14, 2019
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 0947-6539
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 24
Issue 51
Pages 13432-13436
DOI https://doi.org/10.1002/chem.201803574
Keywords allylation, chain walking, homogenous catalysis, isomerization, rhodium
Public URL http://eprints.nottingham.ac.uk/id/eprint/53051
Publisher URL https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201803574
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf
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.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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