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Nickel‐Catalyzed Intermolecular [3+2+2] and [2+2+2] Cocyclizations of Bicyclopropylidene and Alkynes
Author(s) -
Zhao Ligang,
de Meijere Armin
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600348
Subject(s) - chemistry , alkyne , catalysis , intermolecular force , yield (engineering) , nickel , propargyl , molecule , ether , medicinal chemistry , aryl , diene , organic chemistry , stereochemistry , materials science , alkyl , metallurgy , natural rubber
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).