Highly selective synthesis of tetra-substituted furans and cyclopropenes: copper(I)-catalyzed formal cycloadditions of internal aryl alkynes and diazoacetates.
A convenient Cu(I)-catalyzed cycloaddition of electron rich internal aryl alkynes and diazoacetates was discovered for the chemoselective and regioselective synthesis of tetra-substituted furans and cyclopropenes in moderate isolated yields (18-67%), and alkyne conversion (29-73%).
Department of Chemistry, Rochester Institute of Technology, Rochester, NY 14623, USA.
Andrew K
AK
Swenson
Kate E
KE
Higgins
Matthew G
MG
Brewer
William W
WW
Brennessel
Michael G
MG
Coleman
D000085:Acetates / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry
D000085:Acetates; D000480:Alkynes; D001391:Azo Compounds; D003521:Cyclopropanes; D005663:Furans; D009942:Organometallic Compounds; D003300:Copper; C021985:cyclopropene