Environmentally friendly organic synthesis using bismuth(III) compounds.

With increasing environmental concerns, the need for environmentally friendly organic synthesis has gained increased importance. In this regard, bismuth(III) compounds are especially attractive as "green" reagents and catalysts for organic synthesis. Bismuth(III) compounds are remarkably nontoxic, relatively air and moisture stable, and easy to handle.

Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate.

[reaction: see text] Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)(3).xH(2)O (1 < x < 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by in situ generation of the acetal followed by its reaction with allyltrialkylsilane or by a three-component synthesis in which the aldehyde, trimethylorthoformate or an alkoxytrimethylsilane and allyltrimethylsilane are mixed together in the presence of bismuth triflate (0.

Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate.

The chemoselective allylation of acetals using allyltrimethylsilane in ionic liquids is catalyzed by TMS triflate (5.0-20.0 mol %).

A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate.

Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3.4H2O.

A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate.

Bismuth triflate is a highly efficient catalyst (0.1-1 mol %) for the deprotection of acetals and ketals. The procedure is very facile and selective for acetals derived from ketones and conjugated aldehydes.