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

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 Introduction2 Synthesis of Arenecarboxamides3 Synthesis of Alkanamides4 Synthesis of Cyclic Amides5 Formation of Alkynamides6 Formation of Acrylamide-like Molecules7 Formation of Ureas and Carbamates8 Conclusion

The Dark Side of Isocyanides: Visible-Light Photocatalytic Activity in the Oxidative Functionalization of C(sp3)–H Bonds

“…Interestingly, the test reaction of isocyanide 1 with DMA in MeCN at room temperature and under irradiation with 30 W blue light-emitting diodes (LEDs), open in air and in the presence of 10 equivalents of water, led to the formation of amide 2 in 20% yield ( Scheme 1 ). 36 …”

Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides

“… 7 Owing to the practicality and commercial accessibility of their compounds, isocyanides and π systems have been demonstrated to be attractive functionalities for heterocyclic cycloaddition reactions that due to appropriate atom-economy are considered as an ideal approach for the direct synthesis of substituted pyrroles. 8 …”