Recent Advances in the Chemistry of Heavier Group 14 Analogues of Carbonyls.

Heavier analogues of carbonyls, in the form of "R E=O" (E=Si, Ge, Sn, Pb), feature a high polar E=O double bond. In contrast to carbonyl compounds, heavier analogues are extremely unstable and prone to proceed head-to-tail oligomerization. Thus, the isolation of such species under ambient conditions is a challenging synthetic target in main group chemistry. In recent years, much progress has been achieved in the synthesis and isolation of a variety of Lewis base/acid, Lewis base-stabilized and even Lewis acid/base free heavier analogues. These compounds exhibit interesting reactivities, such as small molecule activation and metathesis reactions, indicating the potential of heavier analogues in synthetic chemistry. This review summarizes the recent achievements in the chemistry of Lewis base and/or acid stabilized heavier analogues of carbonyls, including synthetic approaches, structural parameters and reactivity of these isolable compounds.