doi: 10.1002/anie.201701579.
Epub 2017 Apr 10.
Rhodium-Catalyzed meta-C-H Functionalization of Arenes
Affiliations
- PMID: 28393438
- DOI: 10.1002/anie.201701579
Item in Clipboard
Rhodium-Catalyzed meta-C-H Functionalization of Arenes
Angew Chem Int Ed Engl.
.
Abstract
Rhodium-catalyzed ortho-C-H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C-H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.
Keywords: C−H activation; reaction kinetics; reaction mechanisms; regioselectivity; rhodium.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Rhodium catalyzed template-assisted distal para-C-H olefination.Chem Sci. 2019 Jun 21;10(31):7426-7432. doi: 10.1039/c9sc01824g. eCollection 2019 Aug 21. Chem Sci. 2019. PMID: 31489165 Free PMC article.
-
Rhodium-catalyzed atroposelective access to trisubstituted olefins via C-H bond olefination of diverse arenes.Chem Sci. 2023 Jul 3;14(29):7999-8005. doi: 10.1039/d3sc02714g. eCollection 2023 Jul 26. Chem Sci. 2023. PMID: 37502336 Free PMC article.
-
Directing group assisted para-selective C-H alkynylation of unbiased arenes enabled by rhodium catalysis.Chem Sci. 2023 Sep 20;14(41):11381-11388. doi: 10.1039/d3sc03528j. eCollection 2023 Oct 25. Chem Sci. 2023. PMID: 37886091 Free PMC article.
-
Rhodium-Catalyzed C(sp2 )- or C(sp3 )-H Bond Functionalization Assisted by Removable Directing Groups.Angew Chem Int Ed Engl. 2019 Jun 17;58(25):8304-8329. doi: 10.1002/anie.201808159. Epub 2019 Apr 1. Angew Chem Int Ed Engl. 2019. PMID: 30311719 Review.
-
Arene diversification through distal C(sp2)-H functionalization.Science. 2021 May 14;372(6543):eabd5992. doi: 10.1126/science.abd5992. Science. 2021. PMID: 33986152 Review.
Cited by
-
RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group.Chem Sci. 2022 May 30;13(24):7347-7354. doi: 10.1039/d2sc02205b. eCollection 2022 Jun 22. Chem Sci. 2022. PMID: 35799802 Free PMC article.
-
Recent development in transition metal-catalysed C-H olefination.Chem Sci. 2021 Jan 29;12(8):2735-2759. doi: 10.1039/d0sc05555g. Chem Sci. 2021. PMID: 34164039 Free PMC article. Review.
-
Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization.Org Lett. 2020 Nov 6;22(21):8538-8543. doi: 10.1021/acs.orglett.0c03138. Epub 2020 Oct 27. Org Lett. 2020. PMID: 33108197 Free PMC article.
-
Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach.J Am Chem Soc. 2020 Jun 17;142(24):10571-10591. doi: 10.1021/jacs.0c04074. Epub 2020 Jun 5. J Am Chem Soc. 2020. PMID: 32437604 Free PMC article. Review.
-
Rhodium-Catalyzed Oxidative Annulation of 2- or 7-Arylindoles with Alkenes/Alkynes Using Molecular Oxygen as the Sole Oxidant Enabled by Quaternary Ammonium Salt.Molecules. 2021 Sep 2;26(17):5329. doi: 10.3390/molecules26175329. Molecules. 2021. PMID: 34500762 Free PMC article.
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources
