Synthesis of β-Hydroxyl Selenides from Ring-Opening Reaction of Epoxides with ArSeH Catalyzed by ZnCl2

Chinese Journal of Catalysis ›› 2006, Vol. 27 ›› Issue (7): 550-552.

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Synthesis of β-Hydroxyl Selenides from Ring-Opening Reaction of Epoxides with ArSeH Catalyzed by ZnCl2

YANG Minghua1,2*, YANG Hongwei2, ZHENG Yunfa1, ZHU Chengjian2,3

1 Department of Chemistry, Lishui University, Lishui 323000, Zhejiang, China; 2 School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, Jiangsu, China; 3 State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai 200032, China

Received:2006-07-25 Online:2006-07-25 Published:2006-07-25

Abstract

Abstract: ZnCl2-catalyzed selenolysis of epoxides with ArSeH was investigated in ethanol at room temperature. A variety of β-hydroxyl selenides were obtained in excellent yield and good regioselectivity by the simple, efficient and atomic economic procedure. Starting from epoxide o-cresyl glycidyl ether, a one-pot three-step procedure was used for the chemoselective synthesis of N-tosyl-1,3-oxazolidin-2-ones.

Key words: zinc chloride, arylselenol, epoxide, ring-opening reaction, regioselectivity, 1,3-oxazolidin-2-one

YANG Minghua1,2*, YANG Hongwei2, ZHENG Yunfa1, ZHU Chengjian2,3. Synthesis of β-Hydroxyl Selenides from Ring-Opening Reaction of Epoxides with ArSeH Catalyzed by ZnCl2[J]. Chinese Journal of Catalysis, 2006, 27(7): 550-552.

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Synthesis of β-Hydroxyl Selenides from Ring-Opening Reaction of Epoxides with ArSeH Catalyzed by ZnCl2

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