4948-51-0Relevant articles and documents
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Burgstahler,A.W.,Kulier,C.P.
, p. 4384 - 4387 (1965)
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Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study
Han, Bo,Ma, Pengchen,Cong, Xuefeng,Chen, Hui,Zeng, Xiaoming
supporting information, p. 9018 - 9026 (2019/06/13)
Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theoretical mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs.
Catalyzed hydrogenation of condensed three-ring arenes and their N-heteroaromatic analogues by a bis(dihydrogen) ruthenium complex
Borowski, Andrzej F.,Vendier, Laure,Sabo-Etienne, Sylviane,Rozycka-Sokolowska, Ewa,Gaudyn, Alicja V.
, p. 14117 - 14125 (2013/01/15)
A series of anthracene and acridine derivatives were hydrogenated under mild reaction conditions (80 °C, 3 bar of H2) using the bis(dihydrogen) complex [RuH2(η2-H2) 2{P(C6H11)3}2] (1) as a catalyst precursor. The influence of a methyl substituent on the substrate was studied. In all our systems, hydrogenation was only observed at the external rings leading to the corresponding 4H- or 8H-derivatives of anthracene and acridine. Three complexes resulting from the η4(C,C)-coordination of the substrate to the unsaturated fragment [RuH2{P(C 6H11)3}2] were characterized. In the case of 9-methyl acridine, the corresponding complex [RuH2(η 4-C14H11N){P(C6H11) 3}2] (4) turned out to be an active catalyst precursor leading to 1,2,3,4,5,6,7,8-octahydro-9-methylacridine as the sole product after 24 h. Regeneration of 1 from 4 supports the role of complex 4 in the catalytic cycle. Three hydrogenated products, 1,2,3,4-tetrahydroanthracene (4H-Anth), 1,2,3,4-tetrahydro-9-methylanthracene (4H-9-Me-Anth) and 1,2,3,4- tetrahydroacridine (4H-Acr), were characterized by X-ray diffraction. The Royal Society of Chemistry 2012.
