doi: 10.1021/acs.joc.5b02903.
Epub 2016 Feb 5.
Kinetic Control of Rh(III)-Catalyzed Annulation of C-H Bonds with Quinones: Chemoselective Synthesis of Hydrophenanthridinones and Phenanthridinones
Affiliations
- PMID: 26848995
- DOI: 10.1021/acs.joc.5b02903
Item in Clipboard
Kinetic Control of Rh(III)-Catalyzed Annulation of C-H Bonds with Quinones: Chemoselective Synthesis of Hydrophenanthridinones and Phenanthridinones
J Org Chem.
.
Abstract
A temperature-dependent redox-neutral Rh(III)-catalyzed C-H bond annulation of N-methoxybenzamides with quinones was developed for the chemoselective synthesis of hydrophenanthridinones and phenanthridinones. This reaction involves an Rh(III)-catalyzed C-H bond functionalization and a subsequent cyclization through the directing group nucleophilic addition to the carbonyl group at room temperature.
Similar articles
-
Synthesis of Phenanthridinones from N-methoxybenzamides and aryltriethoxysilanes through Rh(III)-catalyzed C-H and N-H bond activation.Chem Asian J. 2013 Sep;8(9):2175-81. doi: 10.1002/asia.201300356. Epub 2013 Jun 7. Chem Asian J. 2013. PMID: 23749384
-
Synthesis of phenanthridinones from N-methoxybenzamides and arenes by multiple palladium-catalyzed C-H activation steps at room temperature.Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9880-3. doi: 10.1002/anie.201104311. Epub 2011 Sep 2. Angew Chem Int Ed Engl. 2011. PMID: 21887827
-
Rh(III)-catalyzed regioselective functionalization of C-H bonds of naphthylcarbamates for oxidative annulation with alkynes.Org Lett. 2014 Sep 19;16(18):4830-3. doi: 10.1021/ol502317c. Epub 2014 Sep 9. Org Lett. 2014. PMID: 25203435
-
Recent advances in Rh(III)/Ir(III)-catalyzed C-H functionalization/annulation via carbene migratory insertion.Org Biomol Chem. 2021 Feb 25;19(7):1438-1458. doi: 10.1039/d0ob02309d. Org Biomol Chem. 2021. PMID: 33508046 Review.
-
Recent advances in the Rh-catalyzed cascade arene C-H bond activation/annulation toward diverse heterocyclic compounds.Org Biomol Chem. 2021 Mar 4;19(8):1705-1721. doi: 10.1039/d0ob02377a. Org Biomol Chem. 2021. PMID: 33537690 Review.
Cited by
-
Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.Org Lett. 2016 Aug 5;18(15):3838-41. doi: 10.1021/acs.orglett.6b01846. Epub 2016 Jul 20. Org Lett. 2016. PMID: 27437933 Free PMC article.
-
Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.Org Lett. 2016 Jul 1;18(13):3294-7. doi: 10.1021/acs.orglett.6b01611. Epub 2016 Jun 23. Org Lett. 2016. PMID: 27337641 Free PMC article.
-
Iridium-catalysed direct sulfamidation of quinazolinones.RSC Adv. 2018 Feb 23;8(16):8450-8454. doi: 10.1039/c8ra00524a. eCollection 2018 Feb 23. RSC Adv. 2018. PMID: 35539849 Free PMC article.
-
Rh(iii)-catalyzed synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones via C-H activation and C-C bond cleavage.RSC Adv. 2022 May 12;12(23):14435-14438. doi: 10.1039/d2ra02074b. eCollection 2022 May 12. RSC Adv. 2022. PMID: 35702227 Free PMC article.
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources
