期刊
TETRAHEDRON
卷 66, 期 44, 页码 8494-8502出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.08.050
关键词
Rhodium (II); Catalysis; Arylation; Boronic acids; N-Heterocycliccarbenes (NHC); Alcohol racemization; DFT calculations
资金
- FCT
- FEDER [SFRH/BD/30619/2006, PTDC/QUI/66695/2006, PTDC/QUI/66015/2006]
- Fundação para a Ciência e a Tecnologia [PTDC/QUI/66695/2006, SFRH/BD/30619/2006] Funding Source: FCT
Here is described the preparation of four new rhodium(II) complexes bearing axial NHC ligands. The presence of electron-withdrawing bridging ligands resulted in an enhanced reactivity in the arylation of aldehydes with boronic acids when compared with the tetraacetate counterparts. Complex 15 (Rh(2)tfa(4)(IPr)(2)) proved to be the most active catalyst for this transformation allowing the selective conversion of aromatic, aliphatic and vinyl aldehydes into the respective alcohols in excellent yields. It was demonstrated that the good group tolerance could be further extended to aromatic and conjugated ketones. DFT calculations carried out on this system showed the complementarily of the bridging ligands and axial ligand in these dinuclear complexes. It was also disclosed that Rh(II)/NHC catalytic system can promote the racemization of 1-phenyl ethanol. (C) 2010 Elsevier Ltd. All rights reserved.
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