Synthesis 2020; 52(06): 819-833
DOI: 10.1055/s-0039-1691561
short review
© Georg Thieme Verlag Stuttgart · New York

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

a  Department of Chemistry, Tamkang University, New Taipei City, 25137, Taiwan, R.O.C.   Email: [email protected]
,
Haw-Lih Su
b  Central Laboratories Unit, Qatar University, Doha, P.O. Box 2713, Qatar
› Author Affiliations
This work was supported by the Ministry of Science and Technology, Taiwan (R.O.C.) (MOST 108-2113-M-032-001).
Further Information

Publication History

Received: 16 November 2019

Accepted after revision: 09 December 2019

Publication Date:
09 January 2020 (online)


Abstract

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 Introduction

2 Nucleophilic Addition of a Nitrile Accelerated by a Lewis Acid

2.1 Late-Transition-Metal Catalysis

2.2 Early-Transition-Metal Catalysis

2.3 Lanthanide-Metal Catalysis

2.4 Cyclization from N-Arylnitriliums

3 Transition-Metal-Catalyzed Insertion of a Nitrile

4 Transition-Metal-Catalyzed Radical Addition of a Nitrile

5 Conclusions

 
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