N-Heterocyclic Carbenes in Late Transition Metal Catalysis

2009 ◽  
Vol 109 (8) ◽  
pp. 3612-3676 ◽  
Author(s):  
Silvia Díez-González ◽  
Nicolas Marion ◽  
Steven P. Nolan
Keyword(s):  
Transition Metal ◽  
Heterocyclic Carbenes ◽  
Transition Metal Catalysis ◽  
Late Transition Metal ◽  
Metal Catalysis ◽  
Late Transition

Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 819-833 ◽  
Author(s):  
Jen-Chieh Hsieh ◽  
Haw-Lih Su
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Nucleophilic Addition ◽  
Radical Addition ◽  
Transition Metal Catalysis ◽  
Late Transition Metal ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Late Transition ◽  
Metal Catalyzed

The diverse methodologies to synthesize N-heterocycles through transition-metal-catalyzed cascade addition/cyclization of a nitrile are discussed in this review. Aspects relating to three types of transition-metal-catalyzed addition of a nitrile with subsequent cyclization include (1) a transition-metal acting as a Lewis acid to accelerate the nucleophilic addition of a nitrile, (2) the late-transition-metal-catalyzed 1,2-insertion of a nitrile, and (3) an in situ generated radical by transition-metal catalysis to implement a radical addition/cyclization tandem reaction. Applications for the synthesis of natural alkaloids, their derivatives, and some bioactive compounds are also summarized herein.1 Introduction2 Nucleophilic Addition of a Nitrile Accelerated by a Lewis Acid2.1 Late-Transition-Metal Catalysis2.2 Early-Transition-Metal Catalysis2.3 Lanthanide-Metal Catalysis2.4 Cyclization from N-Arylnitriliums3 Transition-Metal-Catalyzed Insertion of a Nitrile4 Transition-Metal-Catalyzed Radical Addition of a Nitrile5 Conclusions

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