Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation

Stefan J Pastine; So Won Youn; Dalibor Sames

doi:10.1021/ol034177k

Pt(IV)-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation

Org Lett. 2003 Apr 3;5(7):1055-8. doi: 10.1021/ol034177k.

Authors

Stefan J Pastine¹, So Won Youn, Dalibor Sames

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York 10027, USA.

PMID: 12659572
DOI: 10.1021/ol034177k

Abstract

[reaction: see text] We herein report that PtCl(4) has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.