Studies on Pd/NiFe₂O₄ catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls

• Sanjay R. Borhade and
• Suresh B. Waghmode

Beilstein J. Org. Chem. 2011, 7, 310–319, doi:10.3762/bjoc.7.41

• authors have reported good yields of terphenyls and polyaryls, the fact that the precious palladium catalyst is non-recoverable renders these processes commercially undesirable. The first use of heterogeneous Pd-modified silica catalyst for consecutive Suzuki reactions was reported by Clark et al. for the

Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study

• Benan Kilbas and
• Metin Balci

Beilstein J. Org. Chem. 2011, 7, 246–253, doi:10.3762/bjoc.7.33

• of the palladium catalyst in THF, prepared from tris(dibenzylideneacetone)dipalladium chloroform complex and triisopropyl phosphite. The resulting oxazolidinone 9 was purified by chromatography on a silica gel column to give a crystalline product in 58% yield. The structure and configuration of 9 was

• diacetates 15 and 18b. The isomeric diols 14 and 18a were treated with 2 equiv of toluenesulfonyl isocyanate as described above to give the corresponding biscarbamates 16 and 19. Treatment of 16 and 19 with the palladium catalyst (as described above) resulted in the formation of oxazolidinone derivatives 17

Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF₂

• Lukas J. Gooßen,
• Bettina Zimmermann and
• Thomas Knauber

Beilstein J. Org. Chem. 2010, 6, No. 43, doi:10.3762/bjoc.6.43

• formation of the desired product, albeit in the expected low yields. After some optimization, we were able to convert the electron-poor 2-nitrostilbene (3aa) in high yields even when lowering the palladium catalyst loading from 20 mol % to 5 mol %, and the amount of silver carbonate from 3 to 1.5

• decarboxylated at a palladium catalyst. The coupling of electron-poor 2-nitrobenzoates was achieved by combining a copper-mediated decarboxylation with a palladium-catalyzed Heck coupling. The new mechanistic pathway is likely to open up new perspectives for decarboxylative Heck reactions by overcoming some

Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines

• Susan Kelleher,
• Pierre-Yves Quesne and
• Paul Evans

Beilstein J. Org. Chem. 2009, 5, No. 69, doi:10.3762/bjoc.5.69

• ). Therefore, a one-pot method was developed based on recent reports which demonstrate that the residual palladium catalyst in Heck reactions may effectively mediate the addition of hydrogen to the newly substituted alkene [13][14][15]. Thus, following complete Heck cyclisation, as judged by TLC analysis, the

Oxidative cyclization of alkenols with Oxone using a miniflow reactor

• Yoichi M. A. Yamada,
• Kaoru Torii and
• Yasuhiro Uozumi

Beilstein J. Org. Chem. 2009, 5, No. 18, doi:10.3762/bjoc.5.18

• molecular diffusion path in narrow space reactors often drastically improve the efficiency of a given chemical reaction. As a case in point, we have previously developed a catalyst-installed microflow reactor where a membranous polymeric palladium catalyst was deposited inside a micro-channel reactor at the

Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates

• Jun Xu,
• Xiao-Long Qiu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2008, 4, No. 18, doi:10.3762/bjoc.4.18

• should be temporarily generated once the compounds 1 or 4 were treated with palladium catalyst. Thus, α-substitution products should be afforded considering the steric effects. However, only γ-substitution products 2–3 and 5 were isolated in our case, which, in our opinion, resulted from the specific

Synthesis of the Benzo- fused Indolizidine Alkaloid Mimics

• Daniel L. Comins and
• Kazuhiro Higuchi

Beilstein J. Org. Chem. 2007, 3, No. 42, doi:10.1186/1860-5397-3-42

• . [6][19] In this reaction, only the trans diastereomer was obtained as determined by analysis of the 1H-NMR spectrum of the crude product. This methodology is useful for the synthesis of various types of indolizidine alkaloids and their mimics. Treatment of 1a-i with 5 mol% of palladium catalyst, 2

• %, respectively (entry 1). The reaction in THF with 10 mol% of palladium catalyst at a lower reaction temperature gave 8k in 67% yield (entry 3). [22] Scheme 3 shows a method for substitution at the α-position of N-acyldihydropyridone 11. Our laboratories have reported C-5 substitution of 5-iodo-1,2