Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides

Thirupathi, Nuligonda; Babu, Madala Hari; Dwivedi, Vikas; Kant, Ravi; Reddy, Maddi Sridhar

doi:10.1021/ol501048x

Cited by 84 publications

(19 citation statements)

References 43 publications

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“…In particular, the trifunctionalization of alkynes accompanied by migration provides a platform for the rapid generation of complex molecules with the minimum reaction components and the highest atom‐economy. A few noble metals (Au−, Rh−, Pd− etc.) have been reported to realize alkyne trifunctionalization, however, employment of non‐noble metal such as Cu in this transformation is still underrepresented .…”

Section: Methodsmentioning

confidence: 99%

Copper‐Mediated Cascade Trifunctionalization of N‐Propargylamides

et al. 2019

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The trifunctionalization of alkynes accompanied by intramolecular migration is one of the most powerful tools for rapid enhancing of molecular complexity in synthetic chemistry. Despite significant achievements have been made in the presence of noble metals (such as Au-, Rh-, Pd-, etc.), employment of copper is still underrepresented. Furthermore, 1,1-diiodoalkenes is the core structure of varieties natural products and pharmaceuticals, as well as valuable intermediates for futher manipulations. Herein we report a general and step-economic protocol for the synthesis of 1,1-diiodoalkenes via copper-mediated cascade trifunctionalization of N-propargylamides with halogen sources and tert-butyl nitrite (TBN). This three-component trifunctionalization method enables one-step formation of six new chemical bonds in a high chemo-and regioselective manner. Moreover, the synthesized products have also been selected for evaluation of antitumor activities. One compound was found to display the best potent inhibitory activities against A549, SMMC-7721 and T-24 cells with IC 50 values of 9.16, 23.83 and 18.13 μmol L À 1 . Scheme 1. Trifunctionalization of alkynes for the synthesis of 1,1-Diiodoalkenes (a-b) Previous work. [10] (c) Our copper-mediated cascade trifunctionalization of N-propargylamides.

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Section: Methodsmentioning

confidence: 99%

Copper‐Mediated Cascade Trifunctionalization of N‐Propargylamides

et al. 2019

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“…In this case, the trifluoroacetamide undergoes post-hydrolysis by atmospheric moisture, releasing N-unsubstituted indole derivatives 330. This indole formation was only attempted with tertiary isocyanides [140]. .…”

Section: Scheme 72 Oxidative Pd-catalyzed Formation Of N-acylguanidimentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

et al. 2020

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

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“…Scheme 29 Ag-catalyzed 1,1-aminocarboxamidation of homopropargylamines in the presence of isocyanides Sridhar Reddy and co-workers reported a Pd-catalyzed 1,2-aminocarboxamidation of 1-(o-hydroxy-or 1-(o-aminophenyl)propargylic alcohols 85 with isocyanides yielded benzofuran-2-yl-or indol-2-ylacetamides 86 and 87, respectively (Scheme 30). 85 This approach offers advantages in terms of experimental simplicity, mild reaction conditions, and broad functional group tolerance.…”

Section: Special Topic Synthesismentioning

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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Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides

Cited by 84 publications

References 43 publications

Copper‐Mediated Cascade Trifunctionalization of N‐Propargylamides

Copper‐Mediated Cascade Trifunctionalization of N‐Propargylamides

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

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

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