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Synthesis 2022; 54(01): 4-32
DOI: 10.1055/s-0040-1719831
DOI: 10.1055/s-0040-1719831
review
Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions
We thank the CNRS (Centre National de la Recherche Scientifique) and the MESRI (Ministère de l’Enseignement Supérieur, de la Recherche et de l’Innovation) for financial support. P. M. and S. H. are grateful to Chimie ParisTech for financial support.
Abstract
Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.
1 Introduction
2 Formation of Carbocycles
2.1 Intermolecular Reactions
2.1.1 Cyclotrimerization of Alkynes
2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes
2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides
2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions
2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition
2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition
2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition
2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition
2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition
2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions
3 Formation of Heterocycles
3.1 Cycloaddition of Alkynes with Nitriles
3.2 Cycloaddition of 1,6-Diynes with Cyanamides
3.3 Cycloaddition of 1,6-Diynes with Selenocyanates
3.4 Cycloaddition of Imines with Allenes or Alkenes
3.5 Cycloaddition of (Thio)Cyanates and Isocyanates
3.6 Cycloaddition of 1,3,5-Triazines with Allenes
3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes
3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions
4 Conclusion
Key words
cycloaddition - cyclotrimerization - transition metal - arenes - heterocycles - asymmetric catalysis - alkynes - homogeneous catalysisPublication History
Received: 20 July 2021
Accepted: 29 July 2021
Article published online:
27 September 2021
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