Catalysis continued benzylation

Ag [39], or Au catalysis [40], most protocols continue to call for significant excess ofthe starting alkane relative to oxidant ((5 100 equiv) and the reactions are often limited in scope to benzylic or allylic positions and cyclic ethers. Readily available iminoiodi nanes of formula Phi = NR (R = Ts, Ns) are generally utilized as the source of nitrogen, but the employment of commercially available chloro or broma mine T [34, 37, 41 44] or arylazides [35, 45] has also been reported. 

CsF added to tetra- -butylammonium bromide or Aliquat 336, the mixture stirred for 5 min, n-octyl bromide added, stirring continued for 5 min, and allowed to react for 40 h - n-octyl fluoride. Y 77%. Work-up is easy and reagents readily available yields are high from satd. chlorides and bromides (incl. benzylic), but aromatic bromides were more resistant. F.e. and with tetra-n-butylammonium fluoride, also from tosyla-tes, and comparison with other heterogeneous methods s. G. Bram et al., Synth. Commun. 18, 1661-7 (1988) review of solid-liq. phase transfer catalysis without solvent s. Bull. Soc. Chim. France 1989, 247-51. 

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