Sc(OTf)3-catalyzed synthesis of indoles and SnCl4-mediated regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones

Fang Yang; Ke-Gong Ji; Shaukat Ali; Yong-Min Liang

doi:10.1021/jo201514q

Sc(OTf)3-catalyzed synthesis of indoles and SnCl4-mediated regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones

J Org Chem. 2011 Oct 21;76(20):8329-35. doi: 10.1021/jo201514q. Epub 2011 Sep 16.

Authors

Fang Yang¹, Ke-Gong Ji, Shaukat Ali, Yong-Min Liang

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Chinese Academy of Science, Lanzhou 730000, People's Republic of China.

PMID: 21892834
DOI: 10.1021/jo201514q

Abstract

Highly substituted indole derivatives bearing alkyl and aryl moieties can be prepared by Sc(OTf)(3)-catalyzed Friedel-Crafts alkenylation of 5-(arylamino)pent-3-yn-2-ones. In addition, a method for regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones mediated by SnCl(4) in moderate to good yields (up to 84%) has been developed. The resulting exclusive Z-selectivity of the C-Cl bond can be further exploited using cross C-N coupling reactions.

Publication types

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

MeSH terms

Catalysis
Chemistry, Pharmaceutical / methods*
Halogenation
Indoles / analysis
Indoles / chemical synthesis*
Ketones / chemistry*
Magnetic Resonance Spectroscopy
Mesylates / chemistry*
Molecular Structure
Scandium / chemistry*
Stereoisomerism
Tin Compounds / chemistry*

Substances

Indoles
Ketones
Mesylates
Tin Compounds
scandium triflate
stannic chloride
Scandium