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Aryne–Imine–Aryne Coupling Reaction via [4+2] Cycloaddition between Aza‐ o ‐Quinone Methides and Arynes
Author(s) -
Yoshida Hiroto,
Kuriki Hitoshi,
Fujii Shori,
Ito Yu,
Osaka Itaru,
Takaki Ken
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700251
Subject(s) - aryne , chemistry , cycloaddition , imine , steric effects , quinone , computational chemistry , coupling reaction , combinatorial chemistry , medicinal chemistry , photochemistry , organic chemistry , catalysis
A direct method for the synthesis of acridane derivatives based upon a 2:1 coupling reaction between arynes and imines was developed. The reaction proceeds through formation of transient aza‐ ortho ‐quinone methides arising from a net [2+2] cycloaddition between arynes and imines. Introduction of steric bulk into an imine carbon has proven to be vital for this facile coupling.