Cross-coupling desulfinylative

Scheme 58 Desulfinylative cross-coupling with 2-lhienylsulfinates [356]...

The environmentally benign synthesis of arylated thiophenes 147 in pure water is possible via desulfinylative cross-coupling between nucleophilic 2-thienylsulfinates 146 and differently substituted bromoarenes (Scheme 58, Table 36) [356]. The reaction proceeds efficiently within short reaction times in the presence of tetrakis (triphenylphosphine)palladium(O) (Pd(PPh3)4) without the need for additives, base, cocatalysts, or water-soluble ligands. Additionally, the apphcation of a highly aqueous solvent mixture consisting of water and iV,A -dimethylformamide at a ratio of 3 1... 

In 2005, Liu and Robins showed that the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of arene-boronic acids 121 and 6-[(3-methylbutyl)sulfinyl]purine nucleoside 120 does occur with desulfinylation under suitable conditions as shown here (Scheme 22.35). ... 

SCHEME 22.37. Examples of ligand-less iron-catalyzed desulfinylative C—C cross-coupling reactions of Grignard reagents and sulfonyl chlorides. 

Dubbaka SR, Vogel P. Palladium-catalyzed desulfinylative Negishi C-C bond forming cross-couplings of sulfonyl and organozine chlorides. Tetrahedron Lett. 2006 47(20) 3345-3348. 

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