Abstract
This account describes the recent advances on the Pd-catalyzed [4+2]-benzannulation
reaction, development of chemo- and regiospecific formal [2+2+2]-cyclotrimerization
of alkynes, as well as discovery and evolution of the transition metal-catalyzed cycloisomerization
of alkynyl ketones and imines into five-membered heteroaromatics.
1 Advances in Pd-Catalyzed Benzannulation Reactions
1.1 Introduction
1.2 Formal [2+2+2]-Trimerization of Alkynes
1.3 Acceleration of Benzannulation Reaction by Lewis Acids
1.4 Regioselectivity of the Benzannulation with Unsymmetrical Diynes
1.5 Palladium-Catalyzed Head-to-Head Coupling of Alkynes
1.6 Palladium-Catalyzed Cross-Coupling of Alkynes with Allenes
2 Novel Transition Metal-Catalyzed Cycloisomerization Reactions
2.1 Introduction
2.2 Cu-Catalyzed Cycloisomerization of Alkynyl Imines into Pyrroles
2.3 Cycloisomerization of Alkynyl Ketones into Furans
2.4 Investigation of the Mechanism of the Cu-Catalyzed Cycloisomerization Reaction
2.5 Formation of Unexpected Bicyclic Product
2.6 Multi-Substituted Heterocycles
2.6.1 Towards 3-Substituted Heterocycles
2.6.2 4-Substituted Heterocycles via 1,2-Migrations
2.6.3 Tetrasubstituted Furans
2.7 Fused Pyrroloheterocycles
2.8 Application of the Cycloisomerization Reaction to Synthesis of Alkaloid Structures
3 Conclusion
Key words
transition metal catalysis - benzannulation - cycloisomerization - cascade reactions
- fused heteroaromatics
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