- A Close-to-Aromatize Approach for the Late-Stage Functionalization through Ring Closing Metathesis
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An efficient approach for the synthesis of monosubstituted aromatic compounds relying on a ring-closing metathesis followed by spontaneous 1,2-elimination is presented. The efficiency for late-stage functionalization is highlighted in various solvents (up to 920 TON). This approach is compatible with strained cycles and other multiple bonds in the substrate.
- Lozhkin, Boris,Ward, Thomas R.
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- C-O hydrogenolysis catalyzed by Pd-PMHS nanoparticles in the company of chloroarenes
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Catalytic Pd(OAc)2 and polymethylhydrosiloxane (PMHS), in conjunction with aqueous KF, and a catalytic amount of an aromatic chloride, effects the chemo-, regio-, and stereoselective deoxygenation of benzylic oxygenated substrates at room temperature in THF. Preliminary mechanistic experiments suggest the process to involve palladium-nanoparticle-catalyzed hydrosilylation followed by C-O reduction. The chloroarene additive appears to facilitate the hydrogenolysis process through the slow controlled release of HCl.
- Rahaim, Ronald J.,Maleczka, Robert E.
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supporting information; experimental part
p. 584 - 587
(2011/04/23)
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- Stereoselective synthesis of metalated cyclobutyl derivatives
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Treatment of Z-vinyl carbamates with dicyclopentadienyl(diethyl)zirconium [Et2ZrCp2] leads to cyclobutyl-zirconocene derivatives in good yields and as a unique diastereoisomer. The reaction proceeds through a carbometalative ring-exp
- Tsoglin, Einav,Chechik, Helena,Karseboom, Guy,Chinkov, Nicka,Stanger, Amnon,Marek, Ilan
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supporting information; experimental part
p. 1005 - 1008
(2009/12/05)
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- Zinc-promoted reactions. 8. The effect of ring strain in the reduction of 1,2-dibenzoylcycloalkanes
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Ring cleavage was the main route in the Zn reduction of 1 in neat AcOH, while selective carbonyl reduction predominated in the presence of LiCl. The less strained 2 underwent only carbonyl reduction with Zn/AcOH. The Clemmensen reduction of both 1 and 2 resulted mainly in acyclic products. The unstrained 3 was fairly resistant towards reduction, and did not undergo ring cleavage.
- Di Vona, Maria Luisa,Luchetti, Luciana,Rosnati, Vittorio
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p. 2949 - 2954
(2007/10/02)
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