Palladium(0)-catalyzed regio- and stereoselective addition of heteroatom compounds bearing Si–Se, Ge–Se, and Si–Ge bonds to phenylacetylene

Formation of a Geminal Vinyl Selenide on Selenostannylation of Phenylacetylene under the Action of Stannic Chloride

“…Thus, the regioselectivity of the addition of selanylstannanes II to phenylacetylene is similar to that observed both in nucleophilic additions of arenetholates [3310] and selenolates [11] to terminal acetylenes, which occur mostly as anti-Markovnikov addition [3,7310], or in palladium(0)-catalyzed addition to phenylacetylene of heteroatomic compounds PhSeXMe 3 (X = Si, Ge) and Me 3 GeSiMe 2 Ph [12]. However, unlike the adduct of trimethylsilyl phenyl selenide with phenylacetylene 12], that is resistant to alkali and converts into phenyl 1-phenylvinyl selenide under the action of Bu 4 NF only, our proposed stannylethenyl selenide MeSeCPh= CHSn(SeMe) 3 undergoes destannylation under the action of a dilute solution of KOH.…”

Regio‐ and stereoselective addition of trans‐Pt(TeAr)(SiMe3)(PEt3)2 to terminal alkynes leading to cis‐[(Z)‐β‐trimethylsilylalkenyl]platinum(II) complexes

“…On the other hand, studies dealing with step (ii) or (iii) of the catalytic process are often more complicated and elaborate. Silyl chalcogenides ArESiX 3 (E = S, Se) were able to add to acetylenes in the presence of platinum or palladium catalysts to give the cis adducts with the ArE moiety bound to the internal carbons of the acetylenes [2]), since the generation of R 3 Si[M]EAr ( 1 ) by the oxidative addition of the Si—chalcogen bond to the metal has been well established [3].…”

The Formation of Csp 2 S and Csp 2 Se Bonds by Substitution and Addition Reactions Catalyzed by Transition Metal Complexes

“…Pd(PPh 3 ) 4 catalyst was found to be active in the thioboration [128], thiophosphorylation [129], thioselenation [130], thiosilylation [131] and thiogermanylation [132] reactions. In all of the studied cases the preferred regioselectivity of the addition reaction was to form the R (R 0 S)C¼CHX products (X ¼ B, P, Si, Ge).…”