Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 19, Pages 3332-3340Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700179
Keywords
Triazole; copper; alcohols; dehydrogenation; borrowing hydrogen
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Funding
- National Natural Science Foundation of China [21401080]
- Natural Science Foundation of Jiangsu Province [BK20130125]
- Jiangsu Talents Projec [2013-JNHB-027]
- Fundamental Research Funds for the Central Universities [JUSRP 51627B]
- MOE SAFEA [B13025]
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Triazole-phosphine-copper complexes (TAP-Cu) have been synthesized and applied as tunable and efficient catalysts for the selective synthesis of fluoro-substituted 2-aryl-1H-benzo[d] imidazole and 1-benzyl-2-aryl-1H-benzo[ d] imidazole derivatives from simple alcohols in only one step. TAP-Cu exhibited excellent and tunable catalytic activity for both dehydrogenation and borrowing hydrogen reactions with more than 80 examples being demonstrated for the first time. It was observed that the ligand played a critical role in catalyst activity. Mechanistic studies and deuterium labeling experiments indicated that the reactions proceeded by an initial and reversible alcohol dehydrogenation resulting in a copper hydride intermediate. This was also supported by the direct observation of a diagnostic copper hydride signal by solid-state infrared spectroscopy. The TAP-CuH complex showed absorptions at 912 cm(-1) that could be assigned to copper-hydride stretches. Furthermore, the direct trapping of an intermediate bisimine was also successfully performed.
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