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제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Direct Hydroxylation of Benzene to Phenol Using Hydrogen Peroxide Catalyzed by Nickel Complexes Supported by Pyridylalkylamine Ligands

등록일
2015년 8월 3일 13시 46분 45초
접수번호
0003
발표코드
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발표시간
금 10시 : 15분
발표형식
심포지엄
발표분야
무기화학 - Recent Trends in Bioinorganic Chemistry
저자 및
공동저자
MORIMOTO, Yuma
Osaka University, Japan, Japan
※ 국외소속으로 등록된 저자의 승인여부는 최소 3일이내 발표자 email로 알려드립니다.
승인 1건
Methods for the selective functionalization of aromatic C-H bonds under mild conditions have synthetic applications in the research fields ranging from fine chemistry to industrial scale chemistry. However, direct introduction of oxygen atom into aromatic ring is one of the most challenging chemical reactions due to its notoriously high stability. Thus, development of an efficient method for direct aromatic oxygenation has remained a focal point for extensive research efforts. We report herein aromatic ring hydroxylation with H2O2 employing nickel complexes supported by pyridylalkylamine ligands as catalysts. Among the complexes examined, [NiII(tepa)(OAc)](BPh4) (tepa: tris(2-pyridyl-ethyl)amine, AcO: acetate) has the highest catalytic efficiency for the oxygenation reaction to produce phenol with 21% yield based on benzene. Negligible amount of over oxidation products such as hydroquinone or benzoquinone was yielded, and selectivity for phenol reached to 99% in the system. In endurance test, the catalyst shows the turn over number of 748 in 240 h. A tepa derivative, bepa (N,N-bis[2-(2-pyridyl)ethyl]-2-phenylethylamine) was also found to facilitate this benzene hydroxylation reaction, and we succeeded to observed putative reactive species, dinickel(III)-bis(μ-oxide) complex supported by bepa under low temperature conditions (-60ºC). Adding to this catalytic benzene hydroxylation reaction, we will also discuss substrate scope, effect of the supporting ligand on the efficiency and selectivity of the reaction, and reaction mechanisms in the presentation.

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