Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes

A new functionalization method of arynes promoted by a novel catalytic role of the Grubbs-type ruthenium alkylidene complex is described. Through a sequence of aryne formation followed by their halo-functionalization, various bis-1,3-diynes were directly converted to functionalized aryl chlorides, b...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-06, Vol.14 (21), p.4782-4788
Main Authors: Karmakar, Rajdip, Wang, Kung-Pern, Yun, Sang Young, Mamidipalli, Phani, Lee, Daesung
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Halogenation
Hydrocarbons, Aromatic - chemistry
Organometallic Compounds - chemistry
Ruthenium - chemistry
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Summary:A new functionalization method of arynes promoted by a novel catalytic role of the Grubbs-type ruthenium alkylidene complex is described. Through a sequence of aryne formation followed by their halo-functionalization, various bis-1,3-diynes were directly converted to functionalized aryl chlorides, bromides and iodides in good yields in the presence of a catalytic amount of a ruthenium alkylidene complex and halogenated hydrocarbons such as CH 2 Cl 2 , CHCl 3 , CH 2 Br 2 , and CH 2 I 2 . The utility of this novel transformation is demonstrated by a formal synthesis of herbindole B. A new functionalization method of arynes promoted by a novel catalytic role of the Grubbs-type ruthenium alkylidene complex is described.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob00524a