16928-67-9Relevant academic research and scientific papers
Palladium-catalyzed direct α-arylation of benzyl thioethers with aryl bromides
Frensch, Gustavo,Hussain, Nusrah,Marques, Francisco A.,Walsh, Patrick J.
supporting information, p. 2517 - 2524 (2014/09/29)
The arylation of sp3-hybridized C-H bonds is a powerful strategy to build molecular complexity and diversity. A novel and efficient palladium-catalyzed direct sp3 C-H arylation of aryl and alkyl benzyl thioether derivatives with aryl bromides is reported. The reaction involves reversible deprotonation of the benzylic C-H bond of the thioether with either lithium or sodium bis(trimethylsilyl)amide [LiN(SiMe3)2 or NaN(SiMe3)2] and subsequent cross-coupling to provide the functionalized products in up to 97% yield. A screen of 24 of the most successful ligands in cross-coupling chemistry led to the identification of NiXantPhos as the only viable ligand for this challenging coupling.
Thioalkylation of reactive aromatic compounds with α-(benzotriazol-1-yl)benzyl phenyl sulfide
Katritzky,Xie,Afridi,Fan,Kuzmierkiewicz
, p. 47 - 50 (2007/10/02)
1-[α-(Phenylthio)benzyl]- and 1[(4-methylphenyl)(phenylthio)methyl]benzotriazole, readily available from benzotriazole, an aldehyde and thiophenol, react with a variety of active aromatic compounds under mild conditions to give the thioalkylation products in moderate to good yields.
