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Published on: April 9, 2018
Tetraethylammonium tetraselenotungstate: a versatile selenium transfer reagent in organic synthesis
Devarajulu Sureshkumar1, Purushothaman Gopinath, Srinivasan Chandrasekaran
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, India.
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, [Et(4)N](2)WSe(4) 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 β-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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