Iodine(iii)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes
Literature Information
Publication Date
2016-01-11
DOI
10.1039/C5QO00361J
Impact Factor
5.281
Authors
Christian Depken, Felix Krätzschmar, Alexander Breder
View Original
Abstract
An iodine(III)-mediated synthesis of substituted phenanthrenes from ortho-vinylated biaryl derivatives through highly 6-endo-trig selective oxidative intramolecular arene–alkene coupling is reported. The title method allows for the construction of diversely functionalized target compounds under very mild conditions and in yields ranging up to 79%. Preliminary mechanistic investigations indicate that the reaction presumably proceeds via activation of the alkene moiety followed by a Friedel–Crafts-type electrophilic aromatic substitution at the adjacent arene ring.
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Source Journal
Organic Chemistry Frontiers
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7.8
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8.7%
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724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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