Journal
ACS CATALYSIS
Volume 4, Issue 10, Pages 3581-3585Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs500947d
Keywords
trans-stilbene; diphenylacetylene; hydrogenation; isomerization; intermetallic compound
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Funding
- JSPS KAKENHI [23360353]
- Grants-in-Aid for Scientific Research [23360353] Funding Source: KAKEN
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A series of Rh-based intermetallic compounds supported on silica (RhmMn'/SiO2, M' = Bi, Ge, In, Sb, and Sn) were prepared and tested as catalysts for trans-stilbene (trans-ST) synthesis from diphenylacetylene (DPA) in H-2 atmosphere. Rh2Sb/SiO2 exhibited high catalytic activity in the semihydrogenation of DPA to cis-ST and subsequent isomerization to trans-ST, with a smaller capability of overhydrogenation to diphenylacetylene (DPE) than Rh/SiO2, affording a moderate yield of trans-ST (58%) after complete conversion of DPA. RhSb/SiO2 possesses a unique hydrogenation property capable of half-hydrogenation but minimal overhydrogenation, which enables highly selective isomerization of cis-ST to trans-ST. A tandem catalytic system using RhSb/SiO2 and Pd3Bi/SiO2 afforded 88% yield of trans-ST. These results are the first examples of the effective synthesis of trans-ST from DPA using heterogeneous metallic catalysts.
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