Issue 41, 2019

Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes

Abstract

Terpenes, consisting of isoprene monomer units, represent a family of naturally abundant compounds. The difunctionalization of terpenes is highly appealing yet remains challenging, since the multiple unbiased C[double bond, length as m-dash]C bonds of terpenes lead to difficulty in controlling the regioselectivity. Herein, a cobalt(III)-catalyzed C–H activation strategy has been developed to facilitate hydroxymethylarylation of terpenes with formaldehyde and arenes with high chemo- and regio-selectivities. These (chemo- and regio-) selectivities are governed by the coordination abilities of isoprene, directing groups and the steric effect. This terpene difunctionalization also features high atom and step economy through a C–H addition pathway.

Graphical abstract: Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Jul 2019
Accepted
26 Aug 2019
First published
26 Aug 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 9560-9564

Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes

J. Yang, D. Ji, Y. Hu, X. Min, X. Zhou and Q. Chen, Chem. Sci., 2019, 10, 9560 DOI: 10.1039/C9SC03747K

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