An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C(sp)2-C(sp)3 bond cleavage.
A cool break: 3-Azetidinone and a variety of diynes undergo a cycloaddition reaction catalyzed by Ni/IPr to give dihydroazocine compounds (see scheme; IPr=1,3-bis(2,6-diisopropylphenyl)imidazolidene). The reaction involves a challenging C(sp)2-C(sp)3 bond cleavage step, yet, surprisingly, proceeds at low temperature.
Department of Chemistry, University of Utah, 315 South, 1400 East, Salt Lake City, Utah 84112-0850, USA.
Puneet
P
Kumar
Kainan
K
Zhang
Janis
J
Louie
D000480:Alkynes / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
C116379:2-azetidinone; D000480:Alkynes; D001384:Azetidines; D006571:Heterocyclic Compounds; D009532:Nickel