An Olefin Moiety in the Presence of Terminal Alkyne Function Terminal triple bonds are usually hydrogenated in preference to terminal or internal

In document Nishimura Sh. Handbook of heterogeneous catalytic hydrogenation for organic synthesis (Wiley, 2001)(ISBN 0471396982)(747s).pdf (Page 146-158)

Hydrogenation of Alkenes

Scheme 3.20 Predominant formation of the less stable isomers of saturated ethers in the hydrogenation of methyl-substituted 1-ethoxycyclohexenes over palladium

3.8 SELECTIVE HYDROGENATIONS IN THE PRESENCE OF OTHER FUNCTIONAL GROUPS

3.8.4 An Olefin Moiety in the Presence of Terminal Alkyne Function Terminal triple bonds are usually hydrogenated in preference to terminal or internal

double bonds in competitive conditions, unless the former bonds are highly hindered,

13.5 g (0.065 mol) 60 ml EtOH/80 mg KOH

RT, 1 atm H2, 6.5 h

354 mg (88%) (0.32 + 0.15) g 30% Pd–C

55 ml dioxane/0.5 ml AcOH RT, 1 atm H2, 24 h

because of a strong adsorption of the triple bonds over the double bonds.279 However, Palmer and Casida were successful for selectively hydrogenating such an olefin moi-ety by blocking terminal alkynes with a trimethyl- or triisopropylsilyl group, a bulky and easily removable moiety.280 The compound 125a with an allyl group was thus se-lectively hydrogenated at the olefinic moiety, using 5% Pt–C in dry ethyl acetate con-taining triethylamine to prevent acid-catalyzed trioxabicyclooctane ring opening (eq.

3.83). After the hydrogenation of the olefinic group was complete, some hydrogena-tion of the alkyne group resulted with longer reachydrogena-tion times. Selective hydrogenahydrogena-tion of the compound 125b with a cyclohexenyl moiety was more difficult to achieve, but the desired selectivity was obtained using a more bulky silyl group such as triiso-propylsilyl. Desilylation was accomplished quantitatively with use of tetrabutylam-monium fluoride.

3.8.5 b-Alkoxy-a,b-Unsaturated Ketones (Vinylogous Esters)

The hydrogenation of enol ethers, enol esters, and enol lactones may be accompanied by the hydrogenolysis of the carbon–oxygen bond. The extent of hydrogenolysis greatly depends on the structure of substrate, catalyst, and solvent, as discussed in Sec-tion 13.1.5. Usually the hydrogenolysis occurs most extensively over platinum, and palladium catalysts are preferred for avoiding or minimizing such hydrogenolysis.

<5

3.8 SELECTIVE HYDROGENATIONS IN THE PRESENCE OF OTHER FUNCTIONAL GROUPS 137

The alkoxy group in β-alkoxy-α,β-unsaturated ketones is liable to hydrogenolysis in the hydrogenation to give β-alkoxy ketones, which are also very labile to hydro-genolysis or loss of alcohol to give α,β-unsaturated ketones, especially under acidic conditions or over catalysts containing no alkaline substances. Hydrogenation of the compound 126, however, was successful when THF was used as the solvent instead of ethanol (eq. 3.84).281 Hydrogenation in ethanol led to only vinylogous transesteri-fication product 127.

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