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Preparation of hydrido [CNC]-pincer cobalt complexes via selective C–H/C–F bond activation and their catalytic performances

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Abstract

Polyfluorinated aryl imines 2,4,5-R1,R2,R3-C6H2-HC[double bond, length as m-dash]N-1-C10H7 (R1 = F, R2 = F, R3 = H (1); R1 = F, R2 = H, R3 = F (2) and R1 = F, R2 = F, R3 = F (3)) and F5C6-HC[double bond, length as m-dash]N-1-C10H7 (7) reacted with CoMe(PMe3)4 to give rise to hydrido [CNC]-pincer cobalt(III) complexes (2,4,5-R1,R2,R3-C6H-HC[double bond, length as m-dash]N-1-C10H6)Co(H)(PMe3)2 (R1 = F, R2 = F, R3 = H (4); R1 = F, R2 = H, R3 = F (5); R1 = F, R2 = F, R3 = F (6)) and (F4C6-HC[double bond, length as m-dash]N-1-C10H6)Co(H)(PMe3)2 (8) via selective C–F/C–H bond activation. Penta-coordinate dicarbonyl cobalt(I) complexes (2,4,5-R1,R2,R3-C6H-HC[double bond, length as m-dash]N-1-C10H7)Co(CO)2(PMe3) (R1 = F, R2 = H, R3 = F (9); R1 = F, R2 = F, R3 = F (10)) were obtained from reactions of hexa-coordinate cobalt(III) complexes 5 and 6 with carbon monoxide through reductive elimination. Cobalt(III) halides (2,4,5-R1,R2,R3-C6H-HC[double bond, length as m-dash]N-1-C10H6)Co(I)(PMe3)2 (R1 = F, R2 = F, R3 = H (11); R1 = F, R2 = H, R3 = F (12); R1 = F, R2 = F, R3 = F (13)) and (2,4,5-R1,R2,R3-C6H-HC[double bond, length as m-dash]N-1-C10H6)Co(Br)(PMe3)2 (R1 = F, R2 = F, R3 = H (14); R1 = F, R2 = H, R3 = F (15); R1 = F, R2 = F, R3 = F (16)) were prepared by the interaction between hydrido cobalt(III) complexes 4–6 and MeI or EtBr. The molecular configurations of complexes 4, 8, and 11 were determined by single crystal X-ray diffraction. We then confirmed that the four hydrido cobalt(III) complexes 4–6 and 8 could be used as catalysts for reduction of aldehydes and ketones. Complex 8 is the best catalyst among the four complexes and can selectively catalyze the carbonyl groups of α,β-unsaturated aldehydes and ketones.

Graphical abstract: Preparation of hydrido [CNC]-pincer cobalt complexes via selective C–H/C–F bond activation and their catalytic performances

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Publication details

The article was received on 15 Jun 2018, accepted on 06 Aug 2018 and first published on 07 Aug 2018


Article type: Paper
DOI: 10.1039/C8NJ02979B
Citation: New J. Chem., 2018, Advance Article
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    Preparation of hydrido [CNC]-pincer cobalt complexes via selective C–H/C–F bond activation and their catalytic performances

    F. Yang, Y. Wang, F. Lu, S. Xie, X. Qi, H. Sun, X. Li, O. Fuhr and D. Fenske, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ02979B

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