Synthesis of Organosilatranes via Rhodium(I)-Catalyzed Silylation of Organic Iodides with Hydrosilatrane

Abstract

The silylation of aryl and alkenyl iodides with hydro­silatrane in the presence of a rhodium(I) catalyst and DABCO provides the corresponding organosilatranes in good yield. The same catalyst system also enables the related coupling of hydrogermatrane.

Key words

silicon - rhodium - catalysis - cross-coupling - halides

References

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6

Kishida, E.; Saiki, T.; Ishiyama, T.; Miyaura, N. The 53rd Symposium on Organometallic Chemistry; Osaka, Japan, September 8-9, 2006; Abstract PB253.

10

The results of the silylation of ethyl 4-iodobenzoate with hydrosilatrane (1) in the presence of [Rh(cod)(MeCN)₂]BF₄ and DABCO in selected solvents are as follows [% NMR yield (% conversion)]: DMF, 63 (100); DMSO, 0 (100); MeCN, 0 (100); dioxane, 38 (100); DCE, 0 (8); toluene, trace (27).

13

To some extent, a plausible mechanism for the case of triethoxysilane, proposed by us (see ref. 8b), would refer to the present situation.