Journal ArticleDOI
Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabenzonorbornadienes
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In this paper, the effect of methoxy carbonyl substitution on the C1 position of oxabenzonorbornadienes undergoing palladium-catalyzed nucleophilic ring opening was investigated with a variety of aryl ionics.Abstract:
The effect of ethyl and methoxycarbonyl substitution on the C1 position of oxabenzonorbornadienes undergoing palladium-catalyzed nucleophilic ring opening was investigated with a variety of aryl io...read more
Citations
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Journal ArticleDOI
Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene.
TL;DR: An overview of transition metal-catalyzed reactions from the past couple of years including cobalt, copper, iridium, nickel, palladium and rhodium-catalystzed reactions will be provided, with proposed mechanisms to support the understanding of such reactions.
Journal ArticleDOI
Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes.
Jarvis Hill,William Tam +1 more
TL;DR: The palladium/Lewis acid cocatalyzed ring-opening reaction of various C1-substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated and a mechanism for the formation of C2 regioisomeric ring-opened products has been proposed.
Journal ArticleDOI
Intramolecular Palladium-Catalyzed Ring Opening of Oxabenzonorbornadienes with C1-Tethered Aryl Halides.
TL;DR: The novel intramolecular ring opening of oxabenzonorbornadienes with C1-tethered aryl halides was investigated using palladium catalysts to form fused tetracyclic frameworks, which was generally found to synthesize 1,2-dihydronaphthalen-1-ol products with mild selectivity but was capable of synthesizing dehydrated naphthalene products in excellent yield and selectivity.
Journal ArticleDOI
Iridium-catalyzed ring-opening reactions of unsymmetrical oxabenzonorbornadienes with water and alcohol nucleophiles
TL;DR: The iridium-catalyzed ring-opening reaction of unsymmetrical oxabenzonorbornadienes (OBD) with water and alcohol nucleophiles is reported, with the effects of various C1-substituents explored as discussed by the authors.
References
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Journal ArticleDOI
Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes.
TL;DR: This Account covers the work by the group and by others toward the development of new metal-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.
Journal ArticleDOI
New Catalytic Reactions of Oxa- and Azabicyclic Alkenes
TL;DR: This work has developed several stereo-, regio-, and chemoselective reactions catalyzed by nickel and palladium complexes using these bicyclic alkenes as substrates, providing a unique means of constructing a variety of synthetically useful carbocycles and heterocycles with high efficiency not generally accessible by traditional methods.
Journal ArticleDOI
Scope of palladium-catalyzed alkylative ring opening.
Mark Lautens,Sheldon Hiebert +1 more
TL;DR: The scope of the palladium-catalyzed nucleophilic ring opening methodology has been explored and the addition of various alkyl nucleophiles to oxabenzonorbornadiene has been achieved.
Book ChapterDOI
Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis
Pauline Chiu,Mark Lautens +1 more
TL;DR: In this paper, various methods for the preparation of oxabicyclic compounds, with an emphasis on the stereo and enantioselective synthesis of these substances, are discussed.
Journal ArticleDOI
Mechanistic Studies of the Palladium-Catalyzed Ring Opening of Oxabicyclic Alkenes with Dialkylzinc
TL;DR: The mechanism of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc has been studied in this paper, and it has been shown that a cationic palladium species is responsible for carbopalladation of the alkene.
Related Papers (5)
New Catalytic Reactions of Oxa- and Azabicyclic Alkenes
Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes.
Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes.
Jarvis Hill,William Tam +1 more