Palladium-catalyzed reductive ortho-arylation: evidence for the decomposition of 1,2-dimethoxyethane and subsequent arylpalladium(II) reduction

Andrew Martins; David A Candito; Mark Lautens

doi:10.1021/ol1019037

Palladium-catalyzed reductive ortho-arylation: evidence for the decomposition of 1,2-dimethoxyethane and subsequent arylpalladium(II) reduction

Org Lett. 2010 Nov 19;12(22):5186-8. doi: 10.1021/ol1019037. Epub 2010 Oct 15.

Authors

Andrew Martins¹, David A Candito, Mark Lautens

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

PMID: 20949920
DOI: 10.1021/ol1019037

Abstract

A palladium-catalyzed crossed biaryl coupling/reduction sequence enables the formation of meta-substituted biaryls via solvent-mediated arylpalladium(II) reduction. Isotope labeling studies determined that the decomposition of 1,2-dimethoxyethane (DME) is indeed involved in the reductive process.

Publication types

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

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Ethyl Ethers / chemistry*
Molecular Structure
Oxidation-Reduction
Palladium / chemistry*
Stereoisomerism

Substances

Ethyl Ethers
Palladium
1,2-dimethoxyethane