Novel Methods for the Synthesis of Carbonyl Compounds Based on Decarbonylation of Aldehydes

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  • アルデヒド類の脱カルボニル化を基軸としたカルボニル化合物の新合成法
  • アルデヒドルイ ノ ダツカルボニルカ オ キジク ト シタ カルボニル カゴウブツ ノ シン ゴウセイホウ

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Formyl compounds represent one of synthetic integrants essential for the construction of complex organic molecules. In general, their activation at the carbonyl carbon by a Brønsted or Lewis acid has been used for the new bond formation at the carbon with a wide variety of nucleophiles. On the other hand, transition metal, especially late transition metal, complexes often activate a formyl C-H bond to generate an acylmetal hydride species (RC(=O)-M-H), which can react with a C-C unsaturated bond, leading to the hydroacylation. Furthermore, the C-H bond cleavage, followed by the migratory extrusion of the carbonyl moiety, generates a metal carbonyl species (M-CO) along with the release of R-H. This is recognized as the decarbonylation. The account describes a novel method for synthesis of carbonyl compounds, in which the decarbonylation process of formyl compounds is used as a carbonyl-donating process (CO gas-free carbonylation). It provides more reliable and accessible carbonylation reactions for synthetic organic chemists.

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