Synthesis of aromatic ketones by a transition metal-catalyzed tandem sequence

Jing Zhao; Colin O Hughes; F Dean Toste

doi:10.1021/ja061942s

Synthesis of aromatic ketones by a transition metal-catalyzed tandem sequence

J Am Chem Soc. 2006 Jun 14;128(23):7436-7. doi: 10.1021/ja061942s.

Authors

Jing Zhao¹, Colin O Hughes, F Dean Toste

Affiliation

¹ Department of Chemistry, University of California, Berkeley, California 94720, USA.

PMID: 16756286
DOI: 10.1021/ja061942s

Abstract

Both simple Ag(I) and Au(I) are effective catalysts for a tandem [3,3]-sigmatropic rearrangement/formal Myers-Saito cyclization of propargyl esters to form aromatic ketones. A mechanism in which the metal catalyzes both of these processes through alkyne activation is proposed. By using this method a wide range of aromatic structures including naphthyl, anthracenyl and indole ketones are available from readily available propargyl esters.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Aromatic / chemistry*
Ketones / chemical synthesis*
Magnetic Resonance Spectroscopy
Models, Chemical
Transition Elements / chemistry*

Substances

Hydrocarbons, Aromatic
Ketones
Transition Elements
naphthyl phenyl ketone

Grants and funding

R01 GM073932-01/GM/NIGMS NIH HHS/United States