Stille coupling unactivated secondary alkyl halides

A simple way to avoid toxic and intractable triorganotin waste is to use monoorganotin reagents that are much less toxic and less lipophilic. Unactivated secondary alkyl halides can be coupled with aryl-trichlorotin in a nickel-catalyzed Stille cross-coupling reaction" (e.g. Scheme 5.8.15). 

General procedure for the Stille coupling of unactivated secondary alkyl halides reported by Fu ... 

Powell DA, MaM T, Fu GC. Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents. J. Am. Chem. Soc. 2005 127(2) 510-511. 

The catalyst used is often palladium (0) (like Pd(PPh3)4, Pd2(dba)3), or a source of palladium (II) (like Pd(OAc)2, BnPdCl(PPh3)2 to name a few that gets reduced to the active species palladium(O) in situ. Methods using other metals like manganese, copper, and nickel have been reported the latter has been applied for instance in the successful Stille coupling of unreactive aryl chlorides as well as in the coupling of unactivated primary and secondary alkyl halides. ... 

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