Cross-coupling organomagnesium compounds with

Catalysed cross-coupling of organomagnesium compounds with vinylic and aryl halides... 

Palladium-catalysed cross-coupling of organomagnesium compounds with alkyl halides is rarely useful (e.g. see [36]), but a satisfactory nickel-catalysed coupling with a neopentyl halide has been reported recently [37] ... 

The cross-coupling reaction of (36) and (37) (Scheme 15) with organomagnesium compounds occurs in a similar way, and differs from those above, only in that m these compounds the iodine atom is bonded to the pentacoordinated boron atom in the pentagonal plane. Cross-coupling reactions of organomagnesium compounds with polyhedral B-iodo-substituted compounds containing pentacoordinated boron atoms were previously unknown. 

Transition metal-catalyzed cross-coupling reaction has become the most important method for the formation of aryl-aryl bonds. The reaction of aryl halides and sulfonates with organomagnesium compounds is usually referred... 

We have shown for the first time 12 that not only c/oso-carboranes, but also iodo-nido-7,8-dicarbaundecaborates containing an iodine atom in the polyhedral skeleton or in the pentagonal plane of the polyhedron enter into cross-coupling reactions with organomagnesium and organozinc compounds catalyzed by palladium complexes. It is known that ifo-7,8-dicarbaundecaborates are strong BH-acids (pKa = 21.1), due to the presence of the axial hydrogen atom. 

---