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Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles.
Org Lett. 2013 Feb 15; 15(4):788-91.OL

Abstract

An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N-H) indoles and nitriles has been developed. The acylation reaction proceeded well under the Pd(OAc)(2)/2,2'-bipyridine system and with D-(+)-camphorsulfonic acid as the additive. A possible mechanism involving carbopalladation of nitriles and subsequent hydrolysis of ketimines is proposed.

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Authors+Show Affiliations

Jiang TS
CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, PR China.
Wang GW
No affiliation info available

MeSH

CatalysisIndolesMolecular StructureNitrilesPalladium

Pub Type(s)

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

Language

eng

PubMed ID

23350934

Citation

Jiang, Tao-Shan, and Guan-Wu Wang. "Synthesis of 3-acylindoles By Palladium-catalyzed Acylation of Free (N-H) Indoles With Nitriles." Organic Letters, vol. 15, no. 4, 2013, pp. 788-91.
Jiang TS, Wang GW. Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles. Org Lett. 2013;15(4):788-91.
Jiang, T. S., & Wang, G. W. (2013). Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles. Organic Letters, 15(4), 788-91. https://doi.org/10.1021/ol303440y
Jiang TS, Wang GW. Synthesis of 3-acylindoles By Palladium-catalyzed Acylation of Free (N-H) Indoles With Nitriles. Org Lett. 2013 Feb 15;15(4):788-91. PubMed PMID: 23350934.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles. AU - Jiang,Tao-Shan, AU - Wang,Guan-Wu, Y1 - 2013/01/25/ PY - 2013/1/29/entrez PY - 2013/1/29/pubmed PY - 2013/6/26/medline SP - 788 EP - 91 JF - Organic letters JO - Org Lett VL - 15 IS - 4 N2 - An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N-H) indoles and nitriles has been developed. The acylation reaction proceeded well under the Pd(OAc)(2)/2,2'-bipyridine system and with D-(+)-camphorsulfonic acid as the additive. A possible mechanism involving carbopalladation of nitriles and subsequent hydrolysis of ketimines is proposed. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23350934/Synthesis_of_3_acylindoles_by_palladium_catalyzed_acylation_of_free__N_H__indoles_with_nitriles_ L2 - https://doi.org/10.1021/ol303440y DB - PRIME DP - Unbound Medicine ER -