(NHC)CuH-catalyzed entry to allenes via propargylic carbonate S(N)2'-reductions.
The copper hydride-catalyzed S(N)2'-reduction of propargylic carbonates provides an efficient route to functionalized allenes. The method takes advantage of the stabilizing effect of NHC ligands on CuH and combines high reactivity and stereoselectivity with excellent tolerance toward reactive functionalities.
Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.
Carl
C
Deutsch
Bruce H
BH
Lipshutz
Norbert
N
Krause
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000466:Alkadienes; D000480:Alkynes; D002254:Carbonates; C025947:propadiene; D003300:Copper