Carboxamide substituted tetramethylcyclopentadiene - synthesis, characterisation and its iridium(iii) complex catalysed reduction of imines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F22%3A39918913" target="_blank" >RIV/00216275:25310/22:39918913 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2022/DT/D2DT00149G" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2022/DT/D2DT00149G</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d2dt00149g" target="_blank" >10.1039/d2dt00149g</a>
Alternative languages
Result language
angličtina
Original language name
Carboxamide substituted tetramethylcyclopentadiene - synthesis, characterisation and its iridium(iii) complex catalysed reduction of imines
Original language description
The novel dimeric iodo-iridium(iii) complex, [Ir(Cp*CONMe2)I-2](2), (Cp*CONMe2 = eta(5)-N,N-2,3,4,5-hexamethylcyclopenta-2,4-diene carboxamide) bearing an amide moiety within the tetramethylcyclopentadiene ring, has been synthesised and characterised. The ligand Cp*CONMe2 is synthesised as two regioisomers, however the 2-substituted isomer exists as two distinguishable conformers due to restricted rotation about the amide carbonyl carbon and the ring carbon. The relative acidities of Cp*CONMe2 and Cp* are compared by their relative rates of H/D exchange. The iridium complex of N,N-2,3,4,5-hexamethylcyclopenta-2-4-diene carboxamide [IrCp*CONMe2] and (R,R)-1,2-diphenyl-N '-tosylethane-1,2-diamine ((R,R)-TsDPEN) has been evaluated in the transfer hydrogenation of imines under acidic conditions - a 5 : 2 molar ratio of formic acid : triethylamine as the hydride source for the transfer hydrogenation of 1-methyl-3,4-dihydroisoquinoline (DHIQ) and its 6,7-dimethoxy derivative in acetonitrile. A decreasing enantiomeric excess with reaction progress is attributed to different kinetic orders for formation of the two product amine enantiomers. The pseudo zero-order formation of the R-amine may be due to a pre-steady-state formation of the less stable form of the diastereomeric catalyst. By contrast, both enantiomeric amines from 1-fluorinated methyl DHIQs as substrates for reduction are formed by pseudo first-order processes.
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
10403 - Physical chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dalton Transactions
ISSN
1477-9226
e-ISSN
1477-9234
Volume of the periodical
51
Issue of the periodical within the volume
7
Country of publishing house
GB - UNITED KINGDOM
Number of pages
12
Pages from-to
"2696–2707"
UT code for WoS article
000746883700001
EID of the result in the Scopus database
2-s2.0-85124636197