Bis[cyclic (alkyl)(amino)carbene] isomers : Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC)
Abstract
Isomeric bis(aldiminium) salts with a 1,4-cyclohexylene framework were synthesized. The first isolable bis(CAAC) was prepared from the trans-stereoisomer and its ditopic ligand competency was proven by conversion to iridium(I) and rhodium(I) complexes. Upon deprotonation, the cis-isomer yielded an electron rich olefin via a classic, proton-catalyzed pathway. The C[double bond, length as m-dash]C bond formation from the desired cis-bis(CAAC) was shown to be thermodynamically very favorable and to involve a small activation barrier. Compounds that can be described as insertion products of the cis-bis(CAAC) into the E–H bonds of NH3, CH3CN and H2O were also identified.
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Format
Articles
Research article
Published
2022
Series
Subjects
Publication in research information system
Publisher
Royal Society of Chemistry (RSC)
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202205192771Use this for linking
Review status
Peer reviewed
ISSN
1359-7345
DOI
https://doi.org/10.1039/d2cc01476a
Language
English
Published in
Chemical Communications
Citation
- Puerta Lombardi, B. M., Pezoulas, E. R., Suvinen, R. A., Harrison, A., Dubrawski, Z. S., Gelfand, B. S., Tuononen, H. M., & Roesler, R. (2022). Bis[cyclic (alkyl)(amino)carbene] isomers : Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC). Chemical Communications, 58(45), 6482-6485. https://doi.org/10.1039/d2cc01476a
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Funder(s)
European Commission
Funding program(s)
ERC Consolidator Grant
ERC Consolidator Grant
Funded by the European Union. Views and opinions expressed are however those of the author(s) only and do not necessarily reflect those of the European Union or the European Education and Culture Executive Agency (EACEA). Neither the European Union nor EACEA can be held responsible for them.
Additional information about funding
Financial support was provided by the Universities of Calgary and Jyväskylä as well as the Natural Sciences and Engineering Research Council of Canada (NSERC) in the form of Discovery Grant #2019-07195 to R. R. The project received funding from the European Research Council under the EU’s Horizon 2020 programme (grant #772510 to H. M. T.). A. H. and Z. S. D. acknowledge funding from the Canada First Research Excellence Fund (CFREF).
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