Conjugate reduction of α,β-unsaturated carbonyl and carboxyl compounds with poly(methylhydrosiloxane) catalyzed by a silica-supported compact phosphane-copper complex

Advanced Synthesis and Catalysis

Volumn 354, Issue 18, 2012, Pages 3440-3444

  Kawamorita, Soichiro ^a   Yamazaki, Kenji ^a   Ohmiya, Hirohisa ^a   Iwai, Tomohiro ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

conjugate reduction; copper catalysts; heterogeneous catalysis; immobilized ligands

Indexed keywords

EID: 84871095598     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200555     Document Type: Article

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45. t-BuOH was added to enhance the generation of Cu-H. The Cu-enolate intermediate could be protonated by t-BuOH to generate t-BuO-Cu, which is more active to transmetalate with hydrosilane.
46. [3i]).
47. [3g,3i,3k,3n]).
48. 2×toluene (0.5 mol%), and t-BuOK (6 mol%) in THF at room temperature for 4 h afforded 3a in 98% yield (GC, work-up with 2 M aqueous NaOH).
49. [3n]). We confirmed that the reduction of 1a with the BDP-Cu system proceeded in toluene with a full conversion of 1a; however, 3a was obtained in only a low yield (29%) after the neutral work-up.
50. [3n]).