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Issue 7, 2011
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Recent advances in [2+2+2] cycloaddition reactions

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Abstract

The [2+2+2] cycloaddition is an elegant, atom-efficient and group tolerant process for the synthesis of carbo- and heterocycles, mostly aromatic, involving the formation of several C–C bonds in a single step. Cyclotrimerisation is catalyzed by a variety of organometallic complexes, including more than 15 different metals. The aim of this tutorial review is to point out the most recent advances in this field and to encourage the use of this reaction enroute to complex molecules. After summarizing the most common catalysts and reaction conditions generally used, we survey the mechanistic features currently accepted for this reaction. Section 4 covers the scope of the different [2+2+2] cycloaddition versions starting with the cyclotrimerisation of three triple bonds, including nitriles, with especial emphasis on asymmetric reactions that create central, axial or planar chirality. Then, reactions that use double bonds are addressed. Finally, the most outstanding examples of natural products synthesis using [2+2+2] cycloadditions as a key step reported recently are shown.

Graphical abstract: Recent advances in [2+2+2] cycloaddition reactions

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Publication details

The article was received on 31 Jan 2011 and first published on 23 Mar 2011


Article type: Tutorial Review
DOI: 10.1039/C1CS15029D
Citation: Chem. Soc. Rev., 2011,40, 3430-3444
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    Recent advances in [2+2+2] cycloaddition reactions

    G. Domínguez and J. Pérez-Castells, Chem. Soc. Rev., 2011, 40, 3430
    DOI: 10.1039/C1CS15029D

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