2008
DOI: 10.1002/chem.200800535
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Partial Hydrogenation of Alkynes to cis‐Olefins by Using a Novel Pd0–Polyethyleneimine Catalyst

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Cited by 85 publications
(34 citation statements)
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“…The trans counterpart of the resulting diphenylethenyl moiety is related to the fully-methoxylated derivative of resveratrol (3,5,4’-trihydroxystilbene), a compound exhibiting diverse biological activities [2324]. The chemo- and stereoselective semihydrogenation of internal alkynes may be achieved by two main catalytic methods: with molecular hydrogen using Lindlar’s catalyst [2526] or by transfer hydrogenation with hydrogen donors [2728]. Additionally, alkynes undergo reduction with diimide to produce cis -alkenes [29].…”
Section: Resultsmentioning
confidence: 99%
“…The trans counterpart of the resulting diphenylethenyl moiety is related to the fully-methoxylated derivative of resveratrol (3,5,4’-trihydroxystilbene), a compound exhibiting diverse biological activities [2324]. The chemo- and stereoselective semihydrogenation of internal alkynes may be achieved by two main catalytic methods: with molecular hydrogen using Lindlar’s catalyst [2526] or by transfer hydrogenation with hydrogen donors [2728]. Additionally, alkynes undergo reduction with diimide to produce cis -alkenes [29].…”
Section: Resultsmentioning
confidence: 99%
“…[6] As an extension of these methods, we prepared the isolable amine-and sulfur-poisoned catalysts; i.e., the Pd/C-ethylenediamine complex [Pd/C(en)], [7] Pd-polyethyleneimine complex (Pd/PEI). [8] and Pd/C-diphenyl sulfide complex [Pd/CA C H T U N G T R E N N U N G (Ph 2 S)], [9] for the chemoselective hydrogenations (Figure 1). Furthermore, we also developed a silk fibroin, a protein produced by silkworms possessing very few residues of sulfur-containing amino acids, a supported Pd-catalyst, and a Pd-fibroin complex (Pd/Fib), [10] as the selective hydrogenation catalyst of C-C or N-C multiple bonds in the presence of many other reducible functionalities as summarized in Figure 1.…”
Section: Introductionmentioning
confidence: 99%
“…The chemoselective hydrogenation between the nitro groups and multiple bonds as well as azide groups (entries 1-5) was completely achieved. Other reducible functionalities such as the aryl bromide, N-Cbz and benzyl ester were also tolerated under these conditions (entries [6][7][8].…”
Section: Introductionmentioning
confidence: 99%
“…In recent years, application and designing of highly selective catalyst for partial hydrogenation of alkynes has attracted more attention by virtue of its importance in synthesis of intermediate products [5][6][7][8][9] . The Lindlar catalyst (the Pd on the CaCO 3 poisoned with lead (II) acetate) was the first instance of highly selective supported metal catalyst for liquid phase partial hydrogenation of alkynes to alkenes by utilizing of a suitable surface modifier basic compound such as quinoline.…”
Section: Introductionmentioning
confidence: 99%