Nickel-Catalyzed Intermolecular [3+2+2] and [2+2+2] Cocyclizations of Bicyclopropylidene and Alkynes

Under the catalysis of bis(1,5‐cyclooctadiene)nickel(0), Ni(cod)2, in the presence of triphenylphosphane, two molecules of bicyclopropylidene (1) and one molecule of a terminal alkyne 2 at ambient temperature undergo an intermolecular [3+2+2] cocyclization to furnish the bis‐spirocyclopropanated cyc...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2006-11, Vol.348 (16-17), p.2484-2492
Main Authors: Zhao, Ligang, de Meijere, Armin
Format: Article
Language:English
Subjects:
[2+2+2] cocyclization
[3+2+2] cocyclization
homogeneous catalysis
nickel
seven-membered rings
small rings
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Summary:Under the catalysis of bis(1,5‐cyclooctadiene)nickel(0), Ni(cod)2, in the presence of triphenylphosphane, two molecules of bicyclopropylidene (1) and one molecule of a terminal alkyne 2 at ambient temperature undergo an intermolecular [3+2+2] cocyclization to furnish the bis‐spirocyclopropanated cyclopropylidenecycloheptene derivatives 3 in 45–93 % yield (15 examples plus 2 examples with 8 and 25 % yield, respectively). With the same catalyst system, [2+2+2] cocyclizations of two molecules of an arylmethyl (aryl=phenyl, furyl) propargyl ether and one molecule of bicyclopropylidene (1) occur to provide regioisomeric dispiro[2.0.2.4]deca‐7,9‐diene derivatives 9/10 (2 examples, 57 and 44 % yield, respectively).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200600348