Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Pascal Matton; Steve Huvelle; Mansour Haddad; Phannarath Phansavath; Virginie Ratovelomanana-Vidal

doi:10.1055/s-0040-1719831

Synthesis, Table of Contents

Synthesis 2022; 54(01): 4-32
DOI: 10.1055/s-0040-1719831

review

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Pascal Matton

,

Steve Huvelle

,

Mansour Haddad

,

Phannarath Phansavath

,

Virginie Ratovelomanana-Vidal ∗

Abstract

All articles of this category

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 catalysis

Full Text

References

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