Tandem Cyclization of Alkynes via Rhodium Alkynyl and Alkenylidene Catalysis

A rhodium(I)-catalyzed tandem cyclization of alkynes has been developed. The reaction allows for multiple bond formations to occur at both the α- and β-positions of alkynes under mild conditions to yield a variety of fused ring systems as the products. In the presence of triethylamine and the comple...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-11, Vol.128 (46), p.14818-14819
Main Authors: Joo, Jung Min, Yuan, Yu, Lee, Chulbom
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Alkynes - chemistry
Catalysis
Chemistry
Cyclization
Exact sciences and technology
General and physical chemistry
Rhodium - chemistry
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Summary:A rhodium(I)-catalyzed tandem cyclization of alkynes has been developed. The reaction allows for multiple bond formations to occur at both the α- and β-positions of alkynes under mild conditions to yield a variety of fused ring systems as the products. In the presence of triethylamine and the complex derived from [Rh(COD)Cl]2 and P(4-F-C6H4)3, a terminal alkyne is converted to a rhodium alkynyl species which reacts with a tethered alkyl halide at the β-position to provide a β,β-disubstituted alkenylidene complex. The rhodium alkenylidene species then undergoes additional ring closures with a range of pendent functional groups such as alkene, hydroxyl, and phenyl groups through [2 + 2] cycloaddition, nucleophilic addition, and 6π-electrocyclization processes, respectively.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja066374v