Science of Synthesis

Cellnik, T.; Jo, W.; Healy, A., Science of Synthesis Knowledge Updates, (2024) 2, 396.

Tricyclohexylsilaneselenol (‌168‌) can be coupled with aryl halides in the presence of a catalyst formed from palladium(II) acetate and 2-(dicyclohexylphosphino)-2′,6′-diisopropoxybiphenyl (RuPhos; ‌Scheme 63‌). Aryl chlorides are incompatible with this procedure, but aryl bromides and iodides are efficiently converted into selenoacetates ‌169‌ at room temperature by treatment of the tricyclohexyl-protected areneselenol intermediates with tetrabutylammonium fluoride and acetyl chloride. Exceptions to this general trend are substrates possessing a nitro group or an enolizable carbonyl moiety.[‌277‌]

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References