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Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions
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AbstractMetal-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 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion
Georg Thieme Verlag KG
Title: Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions
Description:
AbstractMetal-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 Introduction2 Formation of Carbocycles2.
1 Intermolecular Reactions2.
1.
1 Cyclotrimerization of Alkynes2.
1.
2 [2+2+2] Cycloaddition of Two Different Alkynes2.
1.
3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.
2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.
2.
1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.
2.
2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.
2.
3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.
2.
4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.
2.
5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.
3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.
1 Cycloaddition of Alkynes with Nitriles3.
2 Cycloaddition of 1,6-Diynes with Cyanamides3.
3 Cycloaddition of 1,6-Diynes with Selenocyanates3.
4 Cycloaddition of Imines with Allenes or Alkenes3.
5 Cycloaddition of (Thio)Cyanates and Isocyanates3.
6 Cycloaddition of 1,3,5-Triazines with Allenes3.
7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.
8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion.
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