Skip to Content

Expedient synthesis of phenanthrenes via In(III)-catalyzed 6-exo-dig cycloisomerization.

Expedient synthesis of phenanthrenes via In(III)-catalyzed 6-exo-dig cycloisomerization.

Organic letters (2013-02-05)

Yongseok Kwon, Hyunkyung Cho, Sanghee Kim

ABSTRACT

This paper documents the first example of In(III)-catalyzed selective 6-exo-dig hydroarylation of o-propargylbiaryls and their subsequent double-bond migration to obtain functionalized phenanthrenes. Electron-rich biaryl substrates undergo hydroarylation more effectively, and the substrates with various types of substituents on the alkyne can also be smoothly and selectively converted to phenanthrenes.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Indium, wire, diam. 1.0 mm, 99.995% trace metals basis

Sigma-Aldrich

Indium, foil, thickness 0.5 mm, 99.99% trace metals basis

Sigma-Aldrich

Indium, foil, thickness 1.0 mm, 99.999% trace metals basis

Sigma-Aldrich

Indium, rod, diam. 6 mm, ≥99.999% trace metals basis

Sigma-Aldrich

Indium, foil, thickness 0.25 mm, 99.995% trace metals basis

Sigma-Aldrich

Indium, wire, diam. 1.0 mm, 99.99% trace metals basis

Sigma-Aldrich

Indium, beads, diam. 2-5 mm, ≥99.9% trace metals basis

Sigma-Aldrich

Indium, powder, 99.99% trace metals basis

Sigma-Aldrich

Indium, bars, 99.95%

Sigma-Aldrich

Indium, wire, diam. 0.45-0.55 mm, 99.995% trace metals basis

Sigma-Aldrich

Indium, powder, −100 mesh, 99.99% trace metals basis

Sigma-Aldrich

Indium, beads, diam. 2-5 mm, 99.999% trace metals basis

Sigma-Aldrich

Indium, pieces, 99.99% trace metals basis

Sigma-Aldrich

Indium, foil, thickness 0.127 mm, 99.99% trace metals basis

Sigma-Aldrich

Indium, foil, thickness 0.25 mm, 99.99% trace metals basis

Sigma-Aldrich

Indium, foil, thickness 0.1 mm, ≥99.995% trace metals basis

Sigma-Aldrich

Indium, wire, diam. 2.0 mm, 99.995% trace metals basis