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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Lepetit, Christine Zargarian, Davit Canac, Yves Duhayon, Carine Chauvin, Remi Vabre, Boris |
| Description | Author Affiliation: Vabre B ( Département deâ chimie, Université deâ Montréal, Montréal (Québec), H3C 3J7 (Canada).); Canac Y ( Laboratoire deâ Chimie deâ Coordination (LCC), CNRS, 205 Route deâ Narbonne, 31077 Toulouse (France). yves.canac@lcc-toulouse.fr.); Lepetit C ( Université deâ Toulouse, UPS, INP, LCC, 31077 Toulouse (France). yves.canac@lcc-toulouse.fr.); Duhayon C ( Laboratoire deâ Chimie deâ Coordination (LCC), CNRS, 205 Route deâ Narbonne, 31077 Toulouse (France). christine.lepetit@lcc-toulouse.fr.); Chauvin R ( Université deâ Toulouse, UPS, INP, LCC, 31077 Toulouse (France). christine.lepetit@lcc-toulouse.fr.); Zargarian D ( Laboratoire deâ Chimie deâ Coordination (LCC), CNRS, 205 Route deâ Narbonne, 31077 Toulouse (France).) |
| Abstract | This contribution reports on a new family of $Ni^{II}$ pincer complexes featuring phosphinite and functional imidazolyl arms. The proligands $^{R}PIMC^{H}OP^{R′}$ react at room temperature with $Ni^{II}$ precursors to give the corresponding complexes $[(^{R}PIMCOP^{R′})NiBr],$ where $^{R}PIMCOP^{R}=κ^{P},κ^{C},κ^{P}-\{2-(R′_{2}PO),6-(R_{2}PC_{3}H_{2}N_{2})C_{6}H_{3}\},$ R=iPr, R′=iPr (3 b, 84 %) or Ph (3 c, 45 %). Selective N-methylation of the imidazole imine moiety in 3 b by MeOTf $(OTf=OSO_{2}CF_{3})$ gave the corresponding imidazoliophosphine $[(^{iPr}PIMIOCOP^{iPr})NiBr][OTf],$ 4 b, in 89 % yield $(^{iPr}PIMIOCOP^{iPr}=κ^{P},κ^{C},κ^{P}-\{2-(iPr_{2}PO),6-(iPr_{2}PC_{4}H_{5}N_{2})C_{6}H_{3}\}).$ Treating 4 b with NaOEt led to the NHC derivative $[(NHCCOP^{iPr})NiBr],$ 5 b, in 47 % yield $(NHCCOP^{iPr}=κ^{P},κ^{C},κ^{C}-\{2-(iPr_{2}PO),6-(C_{4}H_{5}N_{2})C_{6}H_{3})\}).$ The bromo derivatives 3–5 were then treated with AgOTf in acetonitrile to give the corresponding cationic species $[(^{R}PIMCOP^{R})Ni(MeCN)][OTf]$ [R=Ph, 6 a (89 %) or iPr, 6 b (90 %)], $[(^{R}PIMIOCOP^{R})Ni(MeCN)][OTf]_{2}$ [R=Ph, 7 a (79 %) or iPr, 7 b (88 %)], and $[(NHCCOP^{R})Ni(MeCN)][OTf]$ [R=Ph, 8 a (85 %) or iPr, 8 b (84 %)]. All new complexes have been characterized by NMR and IR spectroscopy, whereas 3 b, 3 c, 5 b, 6 b, and 8 a were also subjected to X-ray diffraction studies. The acetonitrile adducts 6–8 were further studied by using various theoretical analysis tools. In the presence of excess nitrile and amine, the cationic acetonitrile adducts 6–8 catalyze hydroamination of nitriles to give unsymmetrical amidines with catalytic turnover numbers of up to 95. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 48 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-11-23 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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