Skip to Content
Merck
CN
  • 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, foil, thickness 0.127 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.25 mm, 99.995% trace metals basis
Sigma-Aldrich
Indium, beads, diam. 2-5 mm, ≥99.9% trace metals basis
Sigma-Aldrich
Indium, powder, −100 mesh, 99.99% trace metals basis
Sigma-Aldrich
Indium, rod, diam. 6 mm, ≥99.999% trace metals basis
Sigma-Aldrich
Indium, bars, 99.95%
Sigma-Aldrich
Indium, wire, diam. 1.0 mm, 99.995% trace metals basis
Sigma-Aldrich
Indium, beads, diam. 2-5 mm, 99.999% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 1.0 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, powder, 99.99% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 0.45-0.55 mm, 99.995% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.25 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.5 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.1 mm, ≥99.995% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 1.0 mm, 99.999% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 2.0 mm, 99.995% trace metals basis