Palladium-Catalyzed Cross-Coupling with Organolithium Reagents

4 Palladium-Catalyzed Cross-Coupling with Organolithium Reagents 

TRANSITION METAL-CATALYZED CARBON-CARBON CROSS-COUPLING 

SCHEME 19.23 (a) and (b) Palladium-catalyzed cross-coupling of organolithium reagents (1979). 

5 Mechanism of Palladium-Catalyzed Cross-Couplings with Rm (m = Li, MgY, ZnY) 

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In 2013, Feringa reported the palladium-catalyzed cross-coupling of organolithium reagents with aryl bromides and chlorides [29]. Pd or Pd° complexes are used associated with bulky electron-rich monophosphines (PfBu, Xphos) or electron-rich NHC ligands (PEPPSI-Ipent) (Scheme 19.24) that favor oxidative additions. 

Murahashi, S.-l. Palladium-catalyzed cross-coupling reaction of organic halides with Grignard reagents, organolithium compounds and heteroatom nucleophiles. J. Organomet. Chem. 2002, 653, 27-33. 

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