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Synlett 2010(20): 2973-2988
DOI: 10.1055/s-0030-1259071
DOI: 10.1055/s-0030-1259071
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New York
Electrophilic Functionalization of Non-Activated Olefins Catalyzed by Lewis Superacids
Further Information
Received
28 July 2010
Publication Date:
24 November 2010 (online)
Publication History
Publication Date:
24 November 2010 (online)
Abstract
The use of metallic triflates and triflimidates as efficient catalysts in recent cycloisomerizations, hydroalkoxylations, hydrocarboxylations, hydrothiolations, Friedel-Crafts reactions, α-amidoalkylation and other C-C, C-O and C-S coupling reactions is reviewed.
1 Introduction
2 Preparation of Metallic Triflates and Triflimidates
2.1 Preparation from Oxides, Halides, Carbonates, and Relatives
2.2 Electrochemical Method
2.3 Oxidative Dissolution of Metallic Powders in the Presence of Superacids
3 Formation of C-C Bonds
3.1 Diels-Alder-Type Reactions
3.2 [3+2] And [2+2] Cycloadditions
3.3 Diene and Polyprenoid Cycloisomerizations
3.4 Friedel-Crafts Reactions
3.4.1 Acylation of Arenes
3.4.2 Alkylation/Benzylation of Arenes
3.4.3 Friedel-Crafts Allylation
3.4.4 Tandem Allylation-Cyclization Processes
3.5 Addition of Nucleophiles to α-Hydroxylactams via N-Acyliminium Ion Intermediates
4 Formation of C-O Bonds
4.1 Intramolecular Hydroalkoxylation of Olefins
4.2 Intermolecular Hydroalkoxylation of Olefins
4.3 Intramolecular Hydrocarboxylation of Olefins
4.4 Dealkylative Cyclization of Epoxy Esters
4.5 Intramolecular Cyclization of Unsaturated Oximes
5 Formation of C-S Bonds
5.1 Intra- and Intermolecular Electrophilic Addition of RSH and RCOSH to Olefins
5.2 Isomerization of Thionolactones to Thiolactones
6 Outlook and Future Prospects
Key words
metallic triflates - metallic triflimidates - carbocations - electrophilic activation
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