Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F19%3A73596999" target="_blank" >RIV/61989592:15310/19:73596999 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlepdf/2019/gc/c9gc00467j" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2019/gc/c9gc00467j</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c9gc00467j" target="_blank" >10.1039/c9gc00467j</a>

Result language
angličtina
Original language name
Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
Original language description
Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromidesand iodides, or dehalogenative sulfonation of (hetero)aryl chlorides andfluorides, using sodium sulfite asthe sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalystand avoids using organic solvent as the reaction medium. This method is especially suitable for substratesthat readily tautomerize (such as 2- or 4-halogenated aminophenols and 4-halogenated resorcinols), forwhich dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfiteis an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three poten-tial applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a redu-cing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardousand corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into lessharmful compounds.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/EG15_019%2F0004431" target="_blank" >EG15_019/0004431: Modern synthetic methods for incoming generics and new drugs under development</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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