Premium
Copper‐Catalyzed Dehydrogenative Cross‐Coupling Reaction between Allylic CH Bonds and α‐CH Bonds of Ketones or Aldehydes
Author(s) -
Huang XingFen,
Salman Muhammad,
Huang ZhiZhen
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402114
Subject(s) - allylic rearrangement , chemistry , catalysis , trifluoromethanesulfonate , coupling reaction , medicinal chemistry , copper , lewis acids and bases , ketone , lewis acid catalysis , aldehyde , organic chemistry , polymer chemistry
A dehydrogenative cross‐coupling reaction between allylic CH bonds and the α‐CH bond of ketones or aldehydes was developed using Cu(OTf) 2 as a catalyst and DDQ as an oxidant. This synthetic approach to γ,δ‐unsaturated ketones and aldehydes has the advantages of broad scope for both ketones and aldehydes as reactants, mild reaction conditions, good yields and atom economy. A plausible mechanism using Cu(OTf) 2 as a Lewis acid catalyst was also proposed (DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone; Tf=trifluoromethanesulfonate).