Frustrated Lewis Pairs Catalyse the Solvent-Assisted Synthesis of Azoles from ortho-Substituted Anilines, CO2 and H2
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F23%3A10468047" target="_blank" >RIV/00216208:11310/23:10468047 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=YnkcRr_oEE" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=YnkcRr_oEE</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cctc.202300510" target="_blank" >10.1002/cctc.202300510</a>
Alternative languages
Result language
angličtina
Original language name
Frustrated Lewis Pairs Catalyse the Solvent-Assisted Synthesis of Azoles from ortho-Substituted Anilines, CO2 and H2
Original language description
Synthesizing azoles from ortho-substituted anilines, CO2 and H2 has proved difficult due to the low nucleophilicity of anilines, which hinders their N-formylation, i. e., the first step of the reaction. This study demonstrates that R(3)SnX Lewis acids (LA), N-methylmorpholine (NMM) or DBU and polyethyleneimine (PEI) or N-formylmorpholine efficiently catalyse the synthesis of benzimidazole and other azoles from ortho-substituted anilines, CO2 and H2 by reductive coupling of CO2 to nucleophilic amine-based solvents, PEI or morpholine, followed by in-situ transfer of the formyl group to the appropriate ortho-substituted aniline. Under these reaction conditions, spontaneous cyclization of the N-formylated intermediate yields the corresponding azole in up to 98 % yield.
Czech name
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Czech description
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Classification
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
10402 - Inorganic and nuclear chemistry
Result continuities
Project
<a href="/en/project/GM21-27431M" target="_blank" >GM21-27431M: Lewis acids and frustrated Lewis pairs for reductive coupling reactions of carbon dioxide with amines</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemCatChem
ISSN
1867-3880
e-ISSN
1867-3899
Volume of the periodical
15
Issue of the periodical within the volume
12
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
e202300510
UT code for WoS article
000987147100001
EID of the result in the Scopus database
2-s2.0-85159321954