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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.

SUBMITTER: Yang J

PROVIDER: S-EPMC6979501 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes.

Yang Jun J Ji Ding-Wei DW Hu Yan-Cheng YC Min Xiang-Ting XT Zhou Xiangge X Chen Qing-An QA

Chemical science 20190826 41

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-sel ...[more]

PMID: 32055328

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