Bis[cyclic (alkyl)(amino)carbene] isomers : Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC)
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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Chemical CommunicationsDate
2022Discipline
Orgaaninen kemiaEpäorgaaninen kemiaNanoscience CenterEpäorgaaninen ja analyyttinen kemiaOrganic ChemistryInorganic ChemistryNanoscience CenterInorganic and Analytical ChemistryCopyright
© Authors, 2022
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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ERC Consolidator Grant
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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 Fi ...
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