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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/EG15_019%2F0004431" target="_blank" >EG15_019/0004431: Moderní metody syntézy pro budoucí generika a nově vyvíjená léčiva</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

GREEN CHEMISTRY

ISSN

1463-9262

e-ISSN

—

Svazek periodika

21

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

2621-2628

Kód UT WoS článku

000468627800029

EID výsledku v databázi Scopus

2-s2.0-85066132416