Selenium–Nitrogen Bond Cleavage in Selenazole Ring System with Grignard Reagent: A Convenient Synthesis of Unsymmetrically Substituted Selenides

Abstract

High reactivity of the selenenamide bond in selenazoles toward nucleophiles can be exploited for synthesis of other organoselenium compounds. It has been found that benzisoselenazol-3(2H)-ones and related selenaheterocycles with an Se-N moiety treated with Grignard reagent gave unsymmetrical aryl-aryl and aryl-alkyl selenides in moderate to good yields. This reaction has a synthetic value because it is highly selective and can be realized under mild conditions.

Keywords:

• Grignard reagents
• heterocycles
• selenenamides
• selenides

ACKNOWLEDGMENTS

The work was supported by the Ministry of Science and Higher Education (Grant 351788/20305).

Notes

^a The yields of selenides 4 when substrates were used in 1:1 molar ratio.