Grignard reagents/palladium chloride

Grignard reagents convert aromatic sulfonyl chlorides or aromatic sulfonates to sulfones. Aromatic sulfonates have also been converted to sulfones with organolithium compounds.1745 Vinylic and allylic sulfones have been prepared by treatment of sulfonyl chlorides with a vinylic or allylic stannane and a palladium-complex catalyst.1746 Alkynyl sulfones can be prepared by treatment of sulfonyl chlorides with trimethylsilylalkynes, with an AICL catalyst.1747... 

Dimethoxy-1 - trimethylstannyl-propane, 118 Grignard reagents, 138 Palladium(II) chloride, 234, Samarium(II) iodide, 270 Titanium(IV) chloride, 304 Cyclopentanones... 

Grignard reagents, 138 Methyl acrylate, 183 Palladium catalysts, 230 Ruthenium(III) chloride, 268 Other methods l-Acetoxy-2,4-hexadiene, 2 Palladium catalysts, 230 Tri-p-carbonylhexacarbonyldiiron, 320... 

A convenient reaction of organolithium with easily available thiuram disulfides was reported by Gronowitz et al. [45], and the reaction of Grignard reagents with N,AT-dimethylthiocarbamoyl chloride was found [46] to be nicely catalysed by NiCl2(dppe) to afford thioamides. An analogous route with palladium[II] catalysis allowed Hartke et al. [47] to prepare a number of interesting a-acetylenic thioamides. 

NHCs are also efficient ligands for the palladium-catalyzed coupling of primary alkyl chlorides with aryl Grignard reagents [99]. Functionalization on both coupling partners is also tolerated in this case. This was due to the mild reaction conditions and fast reaction rates (1 hour of reaction at room temperature). 

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