Tetraethylammonium Tetraselenotungstate: A Versatile Selenium Transfer Reagent in Organic Synthesis

Authors

  • Devarajulu Sureshkumar Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India
  • Purushothaman Gopinath Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India
  • Srinivasan Chandrasekaran Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India

DOI:

https://doi.org/10.2533/chimia.2012.921

Keywords:

Aziridines, Diselenides, Selena-aza-payne and cyclic-diselenides, Selenium, Selenium-transfer reagent, Seleno-cystines, Selenohomocystine, Sugar diselenides, Tetraselenotungstate

Abstract

Organoselenium compounds have attracted intense research owing to their unique biological properties as well as pharmaceutical significance. Progress has been made in developing reagents for incorporation of selenium in an efficient and controlled manner. Herein, we present a review on the recently developed selenium reagent, tetraethylammonium tetraselenotungstate, [Et4N]2WSe4 as a versatile selenium transfer reagent in organic synthesis. Tetraselenotungstate has been successfully used for the synthesis of a number of functionalized diselenides, sugar- and nucleoside-derived diselenides, seleno-cystines, selenohomocystines, selenoamides, selenoureas and sugar- and nucleoside-based cyclic-selenide derivatives. Additionally, this reagent has been employed for the ring opening of aziridines to synthesize a variety of ?-aminodiselenides. A new selena-aza-Payne type rearrangement of aziridinemethanoltosylates mediated by tetraselenotungstate for the synthesis of allyl amines is also discussed.

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Published

2012-12-19

Issue

Section

Scientific Articles

How to Cite

[1]
D. Sureshkumar, P. Gopinath, S. Chandrasekaran, Chimia 2012, 66, 921, DOI: 10.2533/chimia.2012.921.