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Campagne, J.-M.  et al.: 2024 Science of Synthesis, 2024/2: Knowledge Updates 2024/2 DOI: 10.1055/sos-SD-122-00194
Knowledge Updates 2024/2

22.2.5 Selenocarboxylic Acids and Derivatives (Update 2024)

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Book

Editors: Campagne, J.-M. ; Donohoe, T. J.; Jiang, X. ; Wang, M. 

Authors: Cellnik, T. ; de Figueiredo, R. M. ; Deng, G.-J. ; Dong, K. ; Healy, A. ; Huang, H. ; Ji, X. ; Jo, W. ; Manisha ; Murai, T. ; Parmar, D. ; Sawamura, M. ; Sharma, U. ; Shimizu, Y. ; Sumit ; Yang, Z.

Title: Knowledge Updates 2024/2

Online ISBN: 9783132457065; Book DOI: 10.1055/b000000968

1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

Selenocarboxylic acids and their derivatives are the selenium isologues of carboxylic, thioic, carbamic, and carbonic acids, and the corresponding esters, amides, and ureas, and are distinguished by the presence of a C=Se bond. The synthesis of these selenium analogues primarily involves incorporating selenium atoms into precursor molecules. This can be achieved by reducing elemental selenium to produce Se2– species, which are then introduced into electrophilic species. Alternatively, carbon nucleophiles can directly bond with elemental selenium, forming carbon–selenium bonds. Compounds containing a P=Se bond, such as Woollins’ reagent, are used to substitute the oxygen in a C=O bond with selenium, creating a C=Se bond. Carbon diselenide (CSe2) is another agent used in synthesizing these derivatives. However, extreme caution is required when handling CSe2 due to its potent odor and toxicity.

Key words

selenocarboxylic acids - selenocarboxylic acid O-esters - selenocarboxylic acid amides (selenoamides), selenocarbonates, - selenothiocarboxylic acids - diselenocarboxylic acids - selenothioic acid S-esters - selenocarbamate O-esters - selenoureas - diselenocarbonates - diselenocarbamates - diselenothiocabonates - triselenocarbonates - Woollin’s reagent - elemental selenium - carbon diselenide - 2-selenazolines - four-component coupling reactions
 
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