Synthesis 2007(13): 2050-2054  
DOI: 10.1055/s-2007-983739
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Platinum- and Ruthenium-Catalyzed Aromatization of Enediynes via Intramolecular­ Nucleophilic Additions

Bhanu Pratap Taduri, Arjan Odedra, Cheng-Yi Lung, Rai-Shung Liu*
Department of Chemistry, National Tsing-Hua University, 101 Sec 2, Kuang Fu Rd., Hsinchu 30034, Taiwan
e-Mail: rsliu@mx.nthu.edu.tw;
Further Information

Publication History

Received 1 April 2007
Publication Date:
26 June 2007 (online)

Abstract

Catalytic cyclization of enediynes via intramolecular nucleophilic addition was achieved with TpRuPPh3(MeCN)2PF6 and platinum dichloride, giving naphthalene-fused 2,3-dihydrofurans and -pyrroles in good yields. On the basis of experimental results, the mechanism is proposed to involve nucleophilic addition to a π-alkyne intermediate, followed by alkyne insertion.