Palladium-catalyzed synthesis of 2-substituted indoles

Journal Article · Thu Dec 07 23:00:00 EST 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00286a014· OSTI ID:7156397

Rudisill, D E; Stille, J K ^[1]

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1. Colorado State Univ., Fort Collins (USA)

The palladium(0)-catalyzed cross-coupling reaction of alkynylstannanes with 2-bromoanilines or 2-trifloxyanilines results in the formation of 2-alkynylanilines. The coupling reaction tolerates substituents on the anilines, including ester, ether, chloro, and trifloxy groups. A palladium(II)-catalyzed intramolecular cyclization provides 2-substituted indoles. The cyclization proceeds without the need to reoxidize the metal and is most efficient with aliphatic substituents on the alkynyl terminus.

• OSTI ID: 7156397
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:25; ISSN 0022-3263; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKENES
ALKYNES
AMINES
AROMATICS
AZAARENES
AZOLES
CATALYSTS
DATA
DATA ANALYSIS
ELEMENTS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INDOLES
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
METALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PALLADIUM
PLATINUM METALS
PYRROLES
SYNTHESIS
TRANSITION ELEMENTS