Issue 45, 2022

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.

Graphical abstract: Bis[cyclic (alkyl)(amino)carbene] isomers: Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC)

Supplementary files

Article information

Article type
Communication
Submitted
15 Mar 2022
Accepted
27 Apr 2022
First published
18 May 2022
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2022,58, 6482-6485

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

B. M. Puerta Lombardi, E. R. Pezoulas, R. A. Suvinen, A. Harrison, Z. S. Dubrawski, B. S. Gelfand, H. M. Tuononen and R. Roesler, Chem. Commun., 2022, 58, 6482 DOI: 10.1039/D2CC01476A

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