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Benzimidazol-2-ylidene ruthenium complexes for C-N bond formation through alcohol dehydrogenation.
- Source :
- Turkish Journal of Chemistry; 2023, Vol. 47 Issue 5, p1209-1223, 51p
- Publication Year :
- 2023
-
Abstract
- A low temperature hydrogen borrowing approach to generate secondary amines using benzimidazole-based N-heterocyclic carbene (BNHC) ruthenium complexes is reported. A series of the piano-stool complexes of the type [(η<superscript>6</superscript>-p-cymene)(BNHC)RuCl<subscript>2</subscript>] (1a-g) were synthesized via one-pot reaction of the NHC salt precursor, Ag<subscript>2</subscript>O, and [RuCl<subscript>2</subscript>(p-cymene)]<subscript>2</subscript> and characterized using conventional spectroscopic techniques. The geometry of two precursors, [(η<superscript>6</superscript>-p-cymene)(<superscript>Me4Bn</superscript>Me<subscript>2</subscript>BNHC<superscript>CH2OxMe</superscript>)RuCl<subscript>2</subscript>] (1f) and [(η<superscript>6</superscript>-pcymene)(<superscript>Me5Bn</superscript>Me<subscript>2</subscript>BNHC<superscript>CH2OxMe</superscript>)RuCl<subscript>2</subscript>] (1g), was studied by single crystal X-ray diffraction. These catalysts were found to dehydrogenate alcohols efficiently at temperatures as low as 50 °C to allow Schiff-base condensation and subsequent imine hydrogenation to afford secondary amines. Notably, this ruthenium-based procedure enables the N-alkylation of aromatic and heteroaromatic primary amines with a wide range of primary alcohols in excellent yields of up to 98%. The present methodology is green and water is liberated as the sole byproduct. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 13000527
- Volume :
- 47
- Issue :
- 5
- Database :
- Complementary Index
- Journal :
- Turkish Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 173426762
- Full Text :
- https://doi.org/10.55730/1300-0527.3606