A strategy for the cobalt-catalysed allylic fluoroalkylation of terpenes can provide site-selective access to various fluorine-containing motifs under mild conditions. The extension of the protocol to a 2-mol-scale synthesis indicates the scalability of this method.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 digital issues and online access to articles
$119.00 per year
only $9.92 per issue
Rent or buy this article
Prices vary by article type
from$1.95
to$39.95
Prices may be subject to local taxes which are calculated during checkout

References
Newman, D. J., Cragg, G. M. & Snader, K. M. The influence of natural products upon drug discovery. Nat. Prod. Rep. 17, 215–234 (2000). A review article that presents the important role of natural products in drug discovery.
Gillis, E. P., Eastman, K. J., Hill, M. D., Donnelly, D. J. & Meanwell, N. A. Applications of fluorine in medicinal chemistry. J. Med. Chem. 58, 8315–8359 (2015). A review article that presents the tactical applications of fluorine in the design and optimization of drug candidates.
Schrauzer, G. N. & Deutsch, E. Reactions of cobalt(i) supernucleophiles. The alkylation of vitamin B12s, cobaloximes(i), and related compounds. J. Am. Chem. Soc. 91, 3341–3350 (1969). This paper reports that reactions of alkyl halides with Co(i) chelates proceed through an SN2 mechanism, with the Co(i) centres serving as strong nucleophiles.
Wang, S. et al. Site-selective amination towards tertiary aliphatic allylamines. Nat. Catal. 5, 642–651 (2022). This paper reports the site-selective amination of olefins with secondary alkyl amines through cobaloxime-promoted HAT.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
This is a summary of: Wang, S. et al. Cobalt-catalysed allylic fluoroalkylation of terpenes. Nat. Synth. https://doi.org/10.1038/s44160-023-00365-9 (2023).
Rights and permissions
About this article
Cite this article
A strategy for the site-selective allylic fluoroalkylation of terpenes. Nat. Synth (2023). https://doi.org/10.1038/s44160-023-00369-5
Published:
DOI: https://doi.org/10.1038/s44160-023-00369-5