| Title: |
N-Heterocyclic Carbene Analogues of Wittig Hydrocarbon |
| Authors: |
Steffenfauseweh, H.; Vishnevskiy, Y.V.; Neumann, B.; Stammler, H.-G.; de Bruin, B.; Ghadwal, R.S. |
| Source: |
Steffenfauseweh, H, Vishnevskiy, Y V, Neumann, B, Stammler, H-G, de Bruin, B & Ghadwal, R S 2024, 'N-Heterocyclic Carbene Analogues of Wittig Hydrocarbon', Chemistry - A European Journal, vol. 30, no. 26, e202400879. https://doi.org/10.1002/chem.202400879 |
| Publication Year: |
2024 |
| Collection: |
Universiteit van Amsterdam: Digital Academic Repository (UvA DARE) |
| Description: |
N -Heterocyclic carbene (NHC) analogues of Wittig hydrocarbon, [(NHC)(Stil)(NHC)] ( 3a-c ) (NHC = SIPr ( 1a ) = C[N(Dipp)CH 2 ] 2 , Dipp = 2,6-iPr 2 C 6 H 3 ; IPr ( 1b ) = C[N(Dipp)CH] 2 ; Me-IPr ( 1c ) = C[N(Dipp)CMe] 2 and Stil = C 6 H 4 CHCHC 6 H 4 ) have been reported as crystalline solids. 3a-c are prepared by two-electron reductions of the corresponding bis-1,3-imidazoli(ni)um bromides [(NHC)(Stil)NHC)](Br) 2 ( 2a-c ) with KC 8 in >94 % yields. 2a-c are accessible by the nickel catalyzed direct C−C coupling of NHCs ( 1a-c ) with ( E )-4,4'-dibromostilbene. One-electron oxidation of 3a,b yields the corresponding radical cations [(NHC)(Stil)NHC)]B(C 6 F 5 ) 4 4a,b . All compounds have been characterized by UV-Vis/NMR/EPR spectroscopy as well as 2a , 3a , and 3b by single crystal X-ray diffraction. The electronic structures of representative systems have been analyzed by quantum chemical calculations. |
| Document Type: |
article in journal/newspaper |
| File Description: |
application/pdf |
| Language: |
English |
| DOI: |
10.1002/chem.202400879 |
| Availability: |
https://dare.uva.nl/personal/pure/en/publications/nheterocyclic-carbene-analogues-of-wittig-hydrocarbon(6841e097-c47b-4d38-b392-bd37b2a29115).html; https://doi.org/10.1002/chem.202400879; https://hdl.handle.net/11245.1/6841e097-c47b-4d38-b392-bd37b2a29115; https://pure.uva.nl/ws/files/186489843/N-Heterocyclic_Carbene_Analogues_of_Wittig_Hydrocarbon.pdf; https://www.scopus.com/inward/record.uri?eid=2-s2.0-85190514161&doi=10.1002%2fchem.202400879&partnerID=40&md5=7b33c657203a1e3f86e6ee21c34c1787 |
| Rights: |
info:eu-repo/semantics/openAccess |
| Accession Number: |
edsbas.524F5E8D |
| Database: |
BASE |