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Palladium-catalyzed tandem intramolecular oxy/amino-palladation/isocyanide insertion: synthesis of α-benzofuranyl/indolylacetamides.
Org Lett. 2014 Jun 06; 16(11):2908-11.OL

Abstract

A novel palladium-catalyzed approach to 2-benzofuranyl/indolylacetamides from 1-(o-hydroxy/aminophenyl)propargylic alcohols and isocyanides is described. The reaction proceeds through a cascade that includes oxy/aminopalladation, isocyanide insertion, and 1,4-hydroxyl migration. No oxidant or ligand is needed to promote the cascade, and the reactions are carried out under mild conditions to afford the products through high functional tolerance.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Thirupathi N
Medicinal & Process Chemistry Division and §Molecular & Structural Biology Division, CSIR-Central Drug Research Institute , BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.
Babu MH
No affiliation info available
Dwivedi V
No affiliation info available
Kant R
No affiliation info available
Reddy MS
No affiliation info available

MeSH

AcetamidesAlkynesAniline CompoundsBenzofuransCatalysisCyanidesIndolesLigandsMolecular StructurePalladiumPropanols

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24819584

Citation

Thirupathi, Nuligonda, et al. "Palladium-catalyzed Tandem Intramolecular Oxy/amino-palladation/isocyanide Insertion: Synthesis of Α-benzofuranyl/indolylacetamides." Organic Letters, vol. 16, no. 11, 2014, pp. 2908-11.
Thirupathi N, Babu MH, Dwivedi V, et al. Palladium-catalyzed tandem intramolecular oxy/amino-palladation/isocyanide insertion: synthesis of α-benzofuranyl/indolylacetamides. Org Lett. 2014;16(11):2908-11.
Thirupathi, N., Babu, M. H., Dwivedi, V., Kant, R., & Reddy, M. S. (2014). Palladium-catalyzed tandem intramolecular oxy/amino-palladation/isocyanide insertion: synthesis of α-benzofuranyl/indolylacetamides. Organic Letters, 16(11), 2908-11. https://doi.org/10.1021/ol501048x
Thirupathi N, et al. Palladium-catalyzed Tandem Intramolecular Oxy/amino-palladation/isocyanide Insertion: Synthesis of Α-benzofuranyl/indolylacetamides. Org Lett. 2014 Jun 6;16(11):2908-11. PubMed PMID: 24819584.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed tandem intramolecular oxy/amino-palladation/isocyanide insertion: synthesis of α-benzofuranyl/indolylacetamides. AU - Thirupathi,Nuligonda, AU - Babu,Madala Hari, AU - Dwivedi,Vikas, AU - Kant,Ruchir, AU - Reddy,Maddi Sridhar, Y1 - 2014/05/12/ PY - 2014/5/14/entrez PY - 2014/5/14/pubmed PY - 2014/10/7/medline SP - 2908 EP - 11 JF - Organic letters JO - Org Lett VL - 16 IS - 11 N2 - A novel palladium-catalyzed approach to 2-benzofuranyl/indolylacetamides from 1-(o-hydroxy/aminophenyl)propargylic alcohols and isocyanides is described. The reaction proceeds through a cascade that includes oxy/aminopalladation, isocyanide insertion, and 1,4-hydroxyl migration. No oxidant or ligand is needed to promote the cascade, and the reactions are carried out under mild conditions to afford the products through high functional tolerance. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24819584/Palladium_catalyzed_tandem_intramolecular_oxy/amino_palladation/isocyanide_insertion:_synthesis_of_α_benzofuranyl/indolylacetamides_ DB - PRIME DP - Unbound Medicine ER -