PtIV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation
Top Cited Papers
- 11 March 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (7), 1055-1058
- https://doi.org/10.1021/ol034177k
Abstract
[reaction: see text] We herein report that PtCl(4) has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.Keywords
This publication has 8 references indexed in Scilit:
- A Short Synthetic Route to (+)-Austamide, (+)-Deoxyisoaustamide, and (+)-Hydratoaustamide from a Common Precursor by a Novel Palladium-Mediated Indole → Dihydroindoloazocine CyclizationJournal of the American Chemical Society, 2002
- PtII-Catalyzed Intramolecular Reaction of Furans with AlkynesAngewandte Chemie International Edition, 2001
- Annulation of Aromatic Imines via Directed C−H Activation with Wilkinson's CatalystJournal of the American Chemical Society, 2001
- Synthesis of Polycyclic Aromatic Hydrocarbons by the Pd-Catalyzed Annulation of AlkynesThe Journal of Organic Chemistry, 1997
- A model for the cyanide form of oxidized cytochrome oxidase: an iron(III)/copper(II) porphyrin complex displaying ferromagnetic couplingJournal of the American Chemical Society, 1984
- Binary halides of platinum: Preparations, thermal decomposition and structural resultsTransition Metal Chemistry, 1975
- Die durch Silberionen katalysierte Umlagerung von Propargyl‐phenylätherHelvetica Chimica Acta, 1973
- Organoplatinum chemistry. Significance of metal-induced carbonium ionsAccounts of Chemical Research, 1973