Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

Morteza Shiri; Noushin Farajinia-Lehi; Parvin Salehi; Zahra Tanbakouchian

doi:10.1055/s-0040-1707357

Synthesis, Table of Contents

Synthesis 2020; 52(21): 3162-3188
DOI: 10.1055/s-0040-1707357

special topic

Recent Advances in Amide Bond Formation

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

Morteza Shiri ∗

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran Email: mshiri@alzahra.ac.ir

^bDepartment of R&D, Pakshoo Industrial Group, Second Alley, Pakistan St., Beheshti Ave., Tehran, Iran

,

Noushin Farajinia-Lehi

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran Email: mshiri@alzahra.ac.ir

,

Parvin Salehi

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran Email: mshiri@alzahra.ac.ir

,

Zahra Tanbakouchian

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran Email: mshiri@alzahra.ac.ir

› Author Affiliations

Abstract

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This paper is dedicated to Emeritus Professor, Dr. Nasser Iranpoor (Shiraz University) on the occasion of his 67^th birthday.

Abstract

The synthesis of amides is a substantial research area in organic chemistry because of their ubiquitous presence in natural products and bioactive molecules. The use of easily accessible isocyanides as amidoyl (carbamoyl) synthons in cross-coupling reactions using transition metal and inner transition metöal catalysts is a current trend in this area. Isocyanides, owing to their coordination ability as a ligand and inherent electronic properties for reactions with various partners, have expanded the potential application of these transformations for the preparation of novel synthetic molecules and pharmaceutical candidates. This review gives an overview of the achievements in isocyanide-based transition metal and inner transition metal catalyzed amide formation and discusses highlights of the proposed distinct mechanisms.

1 Introduction

2 Synthesis of Arenecarboxamides

3 Synthesis of Alkanamides

4 Synthesis of Cyclic Amides

5 Formation of Alkynamides

6 Formation of Acrylamide-like Molecules

7 Formation of Ureas and Carbamates

8 Conclusion

Key words

isocyanides - transition metal catalysis - cascade reaction - insertion - amide - cross coupling - multicomponent reaction

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References

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