A1 Journal article (refereed)
Bis[cyclic (alkyl)(amino)carbene] isomers : Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC) (2022)

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

JYU authors or editors

Publication details

All authors or editors: Puerta Lombardi, Braulio M.; Pezoulas, Ethan R.; Suvinen, Roope A.; Harrison, Alexander; Dubrawski, Zachary S.; Gelfand, Benjamin S.; Tuononen, Heikki M.; Roesler, Roland

Journal or series: Chemical Communications

ISSN: 1359-7345

eISSN: 1364-548X

Publication year: 2022

Volume: 58

Issue number: 45

Pages range: 6482-6485

Publisher: Royal Society of Chemistry (RSC)

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/d2cc01476a

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/81139

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.

Keywords: isomerism; chemical compounds

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Ministry reporting: Yes

Reporting Year: 2022

JUFO rating: 2