Dimethyl(2-pyridyl)silyl Compounds

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⁾