Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: the isocyano group as an N1 synthon

Liu, Jianquan; Shen, Xuanyu; Liu, Zhenhua; Wang, Xiang‐Shan

doi:10.1039/c7ob01449j

Cited by 14 publications

(6 citation statements)

References 45 publications

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“…Recently, several (boron-based) organo- and transition metal catalysts have also been explored to achieve the direct amidation of carboxylic acids with amines. , However, simultaneous removal of water is required to achieve full conversion. Many other interesting procedures have been developed from precursors other than amines and/or carboxylic acids, such as transamidation, catalytic amidation of unactivated esters, , coupling of (activated) thioacids with amines or azides, catalytic oxidative amidation of aldehydes, , oxidation of in situ -generated aminals from alcohols and amines, aminocarbonylation of alkenes or alkynes, and iodonium-promoted nitroalkane-amine coupling …”

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confidence: 99%

Synthesis of Secondary Amides from Thiocarbamates

et al. 2018

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The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a reactant required for thiocarbamate synthesis. This amide synthesis is suitable for the preparation of challenging amides that are not or hardly accessible via classical approaches.

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confidence: 99%

Synthesis of Secondary Amides from Thiocarbamates

et al. 2018

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“…For this, new reaction pathways from varied starting materials using transition metals as catalysts are being explored . In this context, with aryl isocyanides as an amide source; arenes substituted with leaving groups like halide, diazonium ion, boronic acid and aldehyde have been employed as coupling partners (Scheme (i)). To the best of our knowledge, styrenes have never been used as substrates for the synthesis of N ‐arylbenzamides.…”

Section: Methodsmentioning

confidence: 99%

Chemoselective Synthesis of N‐arylbenzamides and Benzoyloxyacetanilides from Aryl Isocyanides: Styrene as Aryl and Arylcarboxymethylene Source

Sharma

Jain

2018

Adv Synth Catal

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Styrenes serve as unique aryl or arylcarboxymethylene source towards aryl isocyanides in the presence of Cu(II)/TBHP, and yield N-arylbenzamides or benzoyloxyacetanilides respectively. The chemoselectivity of the reaction is controlled by the nature of the substituents present on styrene ring. Whereas styrenes substituted with electronreleasing alkyl and alkoxy groups yield N-arylbenzamides, unsubstituted styrene and those with electron-withdrawing substituents furnish benzoyloxyacetanilides as the major product. With benzylamines as the substrate, N-arylbenzamides are formed exclusively as they act only as an aryl donor. TBHP serves as a promoter and oxygen source. Both the pathways are believed to proceed through an initial oxidative CÀC bond cleavage of styrene.

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“…21 Two synthetic methods for the preparation of amides derived from the Pd-catalyzed reaction of aryl isocyanides with carboxylic acids 22 and Cu-catalyzed reaction of isocyanides with aldehydes have also been described. 23 Interestingly, Zhu and co-workers reported a Pd(II)-catalyzed direct amidation of indoles 5 with isocyanides as a amide source, through a C-H bond activation process at C3, to give indole-3-carboxamides (Scheme 4). 24 The reaction starts with electrophilic palladation at C3 of the indole 5 followed by isocyanide incorporation to generate imidoyl-Pd(II) intermediate 8.…”

Section: Scheme 3 Mn(oac) 3 -Catalyzed Oxidative Coupling Reaction Ofmentioning

confidence: 99%

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

et al. 2020

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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

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Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: the isocyano group as an N1 synthon

Cited by 14 publications

References 45 publications

Synthesis of Secondary Amides from Thiocarbamates

Synthesis of Secondary Amides from Thiocarbamates

Chemoselective Synthesis of N‐arylbenzamides and Benzoyloxyacetanilides from Aryl Isocyanides: Styrene as Aryl and Arylcarboxymethylene Source

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

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