Peterson silyl-Wittig methylenation

The Peterson silyl-Wittig methylenation of carbonyl compounds has been significantly improved by performing the elimination of the trimethylsilanol form of the intermediate /3-hydroxysilanes with Nafion-H under mild conditions1001 [Eq. (5.362)]. 

Olah, G. A., Reddy, V. P., Prakash, G. K. S. Catalysis by solid superacids. 26. Peterson (silyl-Wittig) methylenation of carbonyl compounds using Nafion-H catalyzed hydroxy-trimethylsilane elimination of P-hydroxysilanes. Synthesis 1991,29-30. 

The Peterson reaction has two more advantages over the Wittig reaction 1. it is sometimes less vulnerable to sterical hindrance, and 2. groups, which are susceptible to nucleophilic substitution, are not attacked by silylated carbanions. The introduction of a methylene group into a sterically hindered ketone (R.K. Boeckman, Jr., 1973) and the syntheses of olefins with sulfur, selenium, silicon, or tin substituents (D. Seebach, 1973 B.T. Grdbel, 1974, 1977) illustrate useful applications. The reaction is, however, more limited and time consuming than the Wittig reaction, since metallated silicon derivatives are difficult to synthesize and their reactions are rarely stereoselective (T.H. Chan, 1974 ... 

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