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Dimethyl(2-pyridyl)silyl Compounds
No.120(June 2004)

Yoshida and coworkers have demonstrated that pyridylsilane 1 and 2 can be reacted with tributylstannyl chloride to form a gem-dimetalmethane as a platform for various cross-coupling reactions. In their demonstration, tributylstannyl group is first incorporated into pyridylsilane 1 to make a gem-dimetal, which is then convereted to diarylmethanes 3 by the Stille reaction, followed by the Hiyama reaction.1) In the case of pyridylsilane 2, combination of the Heck reaction and the Hiyama reaction produced multisubstituted olefins 4.2) 1 and 2 can also be utilized in the synthesis of certain alcohols3) and cyclopentenones.4) The additional benefit of using the dimethyl(2-pyridyl)silyl compounds are that they can also be utilized as phase tag as shown in the scheme below. A simple acid-base extraction enables an easy separation/purification of the products feasible.5)

References
- 1)Synthesis of diarylmethanes
- 2)2-Pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis
- 3)(2-Pyridyldimethylsilyl)methyl lithium as a novel hydroxymethylating reagent
- 4)Synthesis of cyclopentenones
- 5)Dual role of 2-pyridyldimethylsilyl group as a directing group and as a phase tag
- 6)Reviews
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