An annulative approach to highly substituted indoles: unusual effect of phenolic additives on the success of the arylation of ketone enolates

Jennifer L Rutherford; Matthew P Rainka; Stephen L Buchwald

doi:10.1021/ja0288993

An annulative approach to highly substituted indoles: unusual effect of phenolic additives on the success of the arylation of ketone enolates

J Am Chem Soc. 2002 Dec 25;124(51):15168-9. doi: 10.1021/ja0288993.

Authors

Jennifer L Rutherford¹, Matthew P Rainka, Stephen L Buchwald

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

PMID: 12487580
DOI: 10.1021/ja0288993

Abstract

A novel palladium-catalyzed arylation of ketone enolates with o-nitrohaloarenes was achieved through the addition of phenol additives. The mild reaction conditions employed allowed for the inclusion of a wide variety of functional groups in both substrates to be tolerated. The products of this reaction were then readily reductively cyclized to give highly substituted indoles in moderate to excellent overall yields.

Publication types

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

MeSH terms

Benzene Derivatives / chemistry
Bromobenzenes / chemistry
Catalysis
Hydrocarbons, Halogenated / chemistry
Indoles / chemical synthesis*
Ketones / chemistry*
Organometallic Compounds / chemistry
Palladium / chemistry
Phenols / chemistry*

Substances

Benzene Derivatives
Bromobenzenes
Hydrocarbons, Halogenated
Indoles
Ketones
Organometallic Compounds
Phenols
Palladium
bromobenzene

Abstract

Publication types

MeSH terms

Substances

Grants and funding