Gold-catalyzed hydroarylation of allenes: a highly regioselective carbon-carbon bond formation producing six-membered rings
- PMID: 17924641
- DOI: 10.1021/ol702179n
Gold-catalyzed hydroarylation of allenes: a highly regioselective carbon-carbon bond formation producing six-membered rings
Abstract
Gold-catalyzed intramolecular hydroarylation of allenic anilines and phenols offers an efficient route to dihydroquinoline and chromene derivatives under mild reaction conditions. The hydroarylation takes place at the terminal or central allenic carbon depending on the substrate structure, leading to a highly selective formation of six-membered rings.
Similar articles
-
Zipper-mode double C-H activation: palladium-catalyzed direct construction of highly-fused heterocyclic systems.Org Lett. 2007 Nov 8;9(23):4813-5. doi: 10.1021/ol702141r. Epub 2007 Oct 9. Org Lett. 2007. PMID: 17924639
-
Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.Org Lett. 2007 May 10;9(10):1935-8. doi: 10.1021/ol070483c. Epub 2007 Apr 12. Org Lett. 2007. PMID: 17428061 Free PMC article.
-
Gold-catalyzed tandem C-C and C-O bond formation: a highly diastereoselective formation of cyclohex-4-ene-1,2-diol derivatives.Org Lett. 2007 Aug 30;9(18):3539-42. doi: 10.1021/ol071402f. Epub 2007 Aug 1. Org Lett. 2007. PMID: 17665922
-
Carbon-CArbon bond formation by Lewis superacid catalysis.Chem Biodivers. 2014 Nov;11(11):1752-63. doi: 10.1002/cbdv.201400020. Chem Biodivers. 2014. PMID: 25408321 Review.
-
Transition metal-catalyzed fluorination of multi carbon-carbon bonds: new strategies for fluorinated heterocycles.Org Biomol Chem. 2012 Aug 21;10(31):6243-8. doi: 10.1039/c2ob25702e. Epub 2012 Jun 26. Org Biomol Chem. 2012. PMID: 22733139 Review.
Cited by
-
Gold(I)-Catalyzed Hydroarylation of Allenes with Indoles.J Organomet Chem. 2009 Feb 15;694(4):571-575. doi: 10.1016/j.jorganchem.2008.11.058. J Organomet Chem. 2009. PMID: 20305794 Free PMC article.
-
Allenamides: a powerful and versatile building block in organic synthesis.Chem Rev. 2013 Jul 10;113(7):4862-904. doi: 10.1021/cr400015d. Epub 2013 Apr 4. Chem Rev. 2013. PMID: 23550917 Free PMC article. Review. No abstract available.
-
Gold(I)-catalyzed intramolecular hydroarylation of allenes.J Org Chem. 2008 Mar 21;73(6):2439-41. doi: 10.1021/jo7024948. Epub 2008 Feb 16. J Org Chem. 2008. PMID: 18278940 Free PMC article.
-
Saucy-Marbet Rearrangements of Alkynyl Halides in the Synthesis of Highly Enantiomerically Enriched Allenyl Halides.Tetrahedron Lett. 2008 Nov 3;49(45):6404-6409. doi: 10.1016/j.tetlet.2008.08.089. Tetrahedron Lett. 2008. PMID: 19890378 Free PMC article.
-
Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitations.Tetrahedron. 2009 Feb;65(9):1785-1789. doi: 10.1016/j.tet.2008.10.110. Tetrahedron. 2009. PMID: 21512612 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources