Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes

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&z.dbd;C bonds of terpenes lead to difficulty in controlling the regioselectivity. Her...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-11, Vol.1 (41), p.956-9564
Main Authors: Yang, Jun, Ji, Ding-Wei, Hu, Yan-Cheng, Min, Xiang-Ting, Zhou, Xiangge, Chen, Qing-An
Format: Article
Language:English
Subjects:
Aromatic compounds
Formaldehyde
Isoprene
Regioselectivity
Terpenes
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Summary: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&z.dbd;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. 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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc03747k