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Journal Name
Green Chemistry
DOI: 10.1039/C4GC02368D
2012, 5, 734; e) naked Fe(0) species: M. Mayer, A. Welther
and A. Jacobi von Wangelin, ChemCatChem, 2011, 3, 1567.
Allylbenzenes were prepared according to: f) M. Mayer, W. M.
Czaplik and A. Jacobi von Wangelin, Adv. Synth. Catal., 2010,
352, 2147.
internal pressure adjusted to 1 bar. After 3ꢀ20 h at room temperature, the
reaction was quenched with saturated aqueous NaHCO3 (1 mL) and
extracted with ethyl acetate (2×2 mL). The organic phases were dried
(Na2SO4) and subjected to flash chromatography (SiO2, pentane/ethyl
acetate) or analyzed by quantitative GCꢀFID analysis vs. pentadecane as
internal reference.
11 a) F. Alonso, I. P. Beletskaya and M. Yus, Chem. Rev., 2002,
102, 4009; b) W. M. Czaplik, S. Grupe, M. Mayer and A.
Jacobi von Wangelin, Chem. Commun., 2010, 46, 6350.
12 D. Gärtner, H. Konnerth and A. Jacobi von Wangelin, Catal.
Sci. Technol., 2013, 3, 2541.
Electronic Supplementary Information (ESI) available: See
DOI: 10.1039/c000000x/
13 a) αꢀMethylstyrene was hydrogenated at 4 bar H2 in the
presence of various functionalized additives (1 equiv.). No
decrease of hydrogenation selectivity was observed when
adding PhCl, PhBr, PhCO2Me, PhNH2, PhCONH2, and 1,1ꢀ
diphenylethylene, respectively. With PhNO2, PhCN, PhI, and
MeCN, no conversion of methylstyrene was observed,
respectively, neither was the additive significantly consumed
(<5%). b) At 1ꢀ2 bar H2, much lower tolerance of functional
groups was observed. We assume that the presence of
functionalized substrates or polar moieties enhances catalyst
ageing and formation of a heterogeneous species which
appeared to somewhat less active. It should also be noted that
sporadic cases of somewhat lower reproducibilities of
reactions at 1 bar H2 pressure were observed with substrates
bearing polar functional groups.
14 NꢀMethylacetamide (AcNHMe), pKa 25.9. F. G. Bordwell, J.
A. Harrelson and T.ꢀY. Lynch, J. Org. Chem., 1990, 55, 3337.
15 NꢀAcetylaminocyclohexenes were prepared according to: a) D.
Strübing, H. Neumann, A. Jacobi von Wangelin, S. Klaus, S.
Hübner and M. Beller, Tetrahedron, 2006, 62, 10962; b) S.
Hübner, H. Neumann, A. Jacobi von Wangelin, S. Klaus, D.
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Klaus, S. Hübner, H. Neumann, D. Strübing, A. Jacobi von
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19 The observation of a partial inhibition by dct results from a
superposition of an effective catalyst inhibition by the presence
of dct and (a slower) hydrogenation of dct as substrate itself
(see entry 27 in table 3).
20 Iron forms only metastable alloys with mercury (amalgam).
The maximum concentration of Fe(0) in Hg was reported to be
2ꢀ3 wt.%. a) S. Mørup, S. Linderoth, J. Jacobsen and M.
Holmblad, Hyperfine Interact., 1991, 69, 489; b) S. Linderoth
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1
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a) P. H. Phua, L. Lefort, J. A. F. Boogers, M. Tristany and
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6
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8
9
a) Technical production and use of H2: H.ꢀJ. Arpe, Industrial
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Please see Supporting Information for detailed experimental
and analytical data.
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