Rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes via successive C-H and C-C bond cleavages
- PMID: 18052297
- DOI: 10.1021/jo7022087
Rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes via successive C-H and C-C bond cleavages
Abstract
The rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes effectively proceeds in a 1:2 manner via cleavage of C-H and C-C bonds to produce the corresponding naphthalene derivatives. Addition of tri- or tetraphenylcyclopentadiene as a ligand is crucial for the reaction to occur efficiently.
Similar articles
-
Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes.Org Lett. 2009 Nov 19;11(22):5198-201. doi: 10.1021/ol9021172. Org Lett. 2009. PMID: 19831368
-
Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage.Chem Commun (Camb). 2009 Sep 14;(34):5141-3. doi: 10.1039/b910198e. Epub 2009 Jul 28. Chem Commun (Camb). 2009. PMID: 20448973
-
Rhodium-catalyzed oxidative coupling/cyclization of 2-phenylindoles with alkynes via C-H and N-H bond cleavages with air as the oxidant.Org Lett. 2010 May 7;12(9):2068-71. doi: 10.1021/ol100560k. Org Lett. 2010. PMID: 20377234
-
Catalytic synthesis of oligoene and enyne derivatives through carbometalation of internal alkynes.Chem Rec. 2008;8(5):326-36. doi: 10.1002/tcr.20158. Chem Rec. 2008. PMID: 18958852 Review.
-
Recent advances in enantioselective [2 + 2 + 2] cycloaddition.Org Biomol Chem. 2008 Apr 21;6(8):1317-23. doi: 10.1039/b720031e. Epub 2008 Mar 12. Org Biomol Chem. 2008. PMID: 18385836 Review.
Cited by
-
Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.Chem Sci. 2012 Jan 1;3(10):3088-3092. doi: 10.1039/C2SC20835K. Epub 2012 Aug 2. Chem Sci. 2012. PMID: 23050074 Free PMC article.
-
The crucial role of silver(I)-salts as additives in C-H activation reactions: overall analysis of their versatility and applicability.Chem Soc Rev. 2023 Sep 18;52(18):6359-6378. doi: 10.1039/d3cs00328k. Chem Soc Rev. 2023. PMID: 37655711 Free PMC article. Review.
-
Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.Acc Chem Res. 2018 Jan 16;51(1):170-180. doi: 10.1021/acs.accounts.7b00444. Epub 2017 Dec 22. Acc Chem Res. 2018. PMID: 29272106 Free PMC article. Review.
-
An Improved Catalyst Architecture for Rhodium (III) Catalyzed C-H Activation and its Application to Pyridone Synthesis.Chem Sci. 2011 Aug 1;2(8):1606-1610. doi: 10.1039/C1SC00235J. Chem Sci. 2011. PMID: 25580208 Free PMC article.
-
Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.J Am Chem Soc. 2017 Jan 25;139(3):1296-1310. doi: 10.1021/jacs.6b11670. Epub 2017 Jan 6. J Am Chem Soc. 2017. PMID: 28060499 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources