Design and Synthesis of Aromatics through [2+2+2] Cyclotrimerization

Abstract

The [2+2+2] cycloaddition reaction is a useful tool to realize unusual chemical transformations which are not achievable by traditional methods. Here, we report our work during the past two decades that involve utilization of transition-metal complexes in a [2+2+2] cyclotrimerization reaction. Several key “building blocks” were assembled by a [2+2+2] cycloaddition approach and they have been further expanded by other synthetic transformations to design unusual amino acids and peptides, diphenylalkanes, bis- and trisaryl benzene derivatives, annulated benzocycloalkanes, spirocycles, and spirooxindole derivatives. Furthermore, we have also discussed about alkyne surrogates, environmentally friendly, and stereoselective [2+2+2] cycloaddition reactions. Application of the [2+2+2] cycloaddition reaction in total synthesis is also covered. In this review we also included others work to give a balanced view of the recent developments in the area of [2+2+2] cycloaddition.

1 Introduction

2 Unusual Amino Acids and Peptides

3 Heteroanalogues of Indane

4 Diphenylalkane Derivatives

5 Multi-Armed Aryl Benzene Derivatives

6 Annulated Benzocycloalkanes

7 Spirocycles

8 Selectivity in [2+2+2] Cycloaddition of Alkynes

9 [2+2+2] Cycloaddition Reactions under Environmentally Friendly Conditions

10 Alkyne Surrogates

11 Domino Reactions involving a [2+2+2] Cycloaddition

12 Biologically Important Targets/Total Synthesis

13 Conclusions

Key words

[2+2+2] cyclotrimerization - Diels–Alder - sultine - amino acids and peptides - spirocycles - Wilkinson’s catalyst - Vollhardt’s catalyst - alkyne surrogates

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