J. Technology and Education, Vol.15, No.1, pp.23-26, 2008

研究論文

電解還元法により発生する硫黄求核種を用いた閉環反応

　

松井栄樹*¹、尾崎茂子²

　

¹福井工業高等専門学校　物質工学科　（〒916-8507　福井県鯖江市下司町）

*eiki@fukui-nct.ac.jp

²大阪大学大学院　薬学研究科　（〒565-0871　大阪府吹田市山田丘1-6）

　

　

Synthesis of Cyclic Sulfides by Nickel(II) Complex-Catalyzed

Intramolecular Cyclization of Thiolates

　

Eiki Matsui¹ and Shigeko Ozaki²

　

¹Department of Chemistry and Biology Engineering, Fukui National College of Technology

(Geshi, Sabae, Fukui 916-8507, Japan)

²Graduate School of Pharmaceutical Sciences, Osaka University

(1-6, Yamadaoka, Suita, Osaka 565-0871, Japan)

　

　

(Received May 20, 2008; Accepted June 6, 2008)

　

　

　　　　　　　　　　　　　　　　　Abstract

　We investigated the intramolecular heterocyclization of thiolates generated in situ by the nickel complex-catalyzed electroreduction of thioacetates. First, functionalized cyclic sulfides with four- to six-membered rings were synthesized by the cyclization of thiolates, which have suitably placed electrophilic olefins or acetylenes. Secondly, five- to seven-membered cyclic sulfides?were synthesized in good to high yields by regioselective epoxide cleavage. These approaches are very mild and convenient, and they are expected to become a general method for the provision of functionalized cyclic sulfides.

Key words: Nickel Complex, Indirect Electroreduction, Thioacetates, Cyclization, Cyclic Sulfides