Palladium- and nickel-catalyzed cross-couplings of unsaturated halides bearing relatively acidic protons with organozinc reagents.
A wide range of polyfunctional aryl, heteroaryl, alkyl, and benzylic zinc reagents were coupled with unsaturated aryl halides bearing an acidic NH or OH proton, using Pd(OAc)2 (1 mol %) and S-Phos (2 mol %) as catalyst without the need of protecting groups. A similar nickel-catalyzed reaction is described. The relative kinetic basicity of organozinc compounds as well as their stability toward acidic protons is also described.
Department Chemie and Biochemie, Ludwig-Maximilians-Universität, Butenandtstr. 5-13, 81377 Munich, Germany.
Georg
G
Manolikakes
Carmen
C
Muñoz Hernandez
Matthias A
MA
Schade
Albrecht
A
Metzger
Paul
P
Knochel
D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D009532:Nickel; D009942:Organometallic Compounds; D010165:Palladium; D015032:Zinc
D003432:Cross-Linking Reagents; D006219:Halogens; D009942:Organometallic Compounds; D010165:Palladium; D009532:Nickel; D015032:Zinc