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Metal-Ligand Cooperation of Cobalt(I) Complexes Bearing a Phenanthroline-Based Tetradentate PNNP Ligand and Its Application to Catalytic Hydrodehalogenation of Aryl Halides

Jheng, Nai-Yuan 筑波大学 DOI:10.15068/0002005515

2022.11.17

概要

Research on catalysts has intensely sprouted in recent years due to reconsideration for over- exhausted resources such as their precious counterparts,1 e.g. complexes of ruthenium, rhodium, and platinum. Therefore, the demand for more sustainable and cheaper surrogates encourages more scientists to develop new catalysts. With similar electronic configurations in valence shells to those of noble metal atoms, 3d metal complexes are considered as candidates to replace those precious metal catalysts. In addition, 3d metal complexes are usually inexpensive, more earth- abundant, and less toxic. Thus, there are recently more and more research focusing on the development of new 3d metal catalysts.

　In the study of these new 3d metal catalysts, cobalt complexes are regarded as one of the most promising systems due to their involvement in various biochemical and catalytic reactions.2 In industries, for example, both Fischer–Tropsch3 and hydroformylation processes4 are well- known cobalt-catalyzed processes. The former often makes use of a metallic cobalt usually supported on ruthenium, alumina, etc. to transform carbon monoxide (CO) and hydrogen (H2) into hydrocarbons. The latter historically applies cobalt tetracarbonyl hydride, [HCo(CO)4], as a catalyst to achieve aldehydes formation from alkenes, CO, and H2. Interestingly, this reaction was discovered by Roelen while he studied the Fisher-Tropsch process in 1938 (Scheme 1).5

　The cobalt complex, [HCo(CO)4], is a well-defined cobalt catalyst, and the widely-accepted mechanism was proposed by Heck and Breslow in 1960.6 It is also widely known that the phosphine-supported Rh(I) complex, [HRh(CO)2(PPh3)2],7 was developed by Wilkinson et al. and revealed to exhibit much higher catalytic performance for the hydroformylation reaction. However, it is worth mentioning that a recent study on cobalt catalyst systems revealed that a cationic cobalt(II) carbonyl hydrido complex bearing two phosphine ligands can approach the performance of the Rh catalyst.8

　Cobalamins (vitamin B12) as an enzyme having a cobalt ion at the active center, which belong to one of B vitamins and cofactors involved in DNA syntheses, nervous systems, and other biological reactions,9 are known to facilitate the generation of alkyl radicals, such as deoxyadenosyl radical via homolysis of a weak CoC bond (ca. 20 ~ 30 kcal/mol) (Scheme 2).10

　Such mechanisms of radical generation by cobalamins and related compounds were applied to reduction of aryl halides, establishing processes for syntheses (i.e. deprotection of halide in aromatic systems)11 and degradation of organic halides, which are common chemical wastes and sources of pollution.12 For example, pentachlorophenol (PCP) can be mainly converted to isomers of tetrachlorophenol by vitamin B12 and titanium(III) citrate at room temperature after 24 hours (Scheme 3).13

　Although there are some practical reactions catalyzed by cobalt complexes, and they are highly expected as candidates of precious metal catalyst surrogates, most of the cobalt complexes still cannot be compatible with other noble metal complexes. Therefore, to overcome the inferiority, suitable ligand designs are desired to further expand the reaction chemistry of cobalt complexes.

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(10) Ishizaka, Y. Master thesis in February 2019.

(11) Jheng, N.Y.; Ishizaka, S.; Naganawa, Y.; Sekiguchi, A.; Nakajima, Y. Dalton Trans. 2020, 49, 14592–14597.

(12) 2H NMR Measurement of 4-d was not successful probably due to the relatively low solubility of 4-d in benzene to afford good resolution.

Chapter 4

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(20) Here Marcus-Hush theory was also applied, ΔG++ = αΔG° + constant, giving α = 0.58. See Figure 7.

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