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Gold and TfOH‐Cocatalyzed Tandem Reaction of ortho ‐Akynylarylaldehydes with Cyclopropenes: an Efficient Route to Functionalized Benzo[7]annulene Derivatives
Author(s) -
Meng Xin,
Guo Minghui,
Zhu Jiekun,
Zhu Hongbo,
Sun Xuejun,
Tian Laijin,
Cao Ziping
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900118
Subject(s) - chemistry , cycloaddition , annulene , tandem , combinatorial chemistry , cleavage (geology) , stereoselectivity , ring (chemistry) , photochemistry , stereochemistry , catalysis , organic chemistry , materials science , geotechnical engineering , fracture (geology) , engineering , composite material
A novel gold(III) and TfOH‐cocatalyzed reaction of ortho ‐alkynylbenzaldehydes with cyclopropenes was described for the synthesis of a variety of functionalized benzo[7]annulene derivatives in a highly stereoselective manner. This reaction could undergo tandem [4+2] cycloaddition/ring expansion to achieve the construction of seven‐membered‐carbocycles, along with the cleavage of double bond of cyclopropenes. The reaction features simple operations, commercially available catalysts and broad substrate scope with good efficiencies.