Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• reaction (pathway A) via ate complex 11a [10] of the electron-rich, more nucleophilic (p-methoxyphenyl)boronic acid (2b), which outcompetes the palladium-catalyzed pathway B (Scheme 2b). In turn, suppression or at least a significant deceleration of the uncatalyzed background reaction should lead to an

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• supramolecular receptors. In particular, we have shown that the 1N,2O-TAAD derivative reacts with phenylboronic acid producing a novel type of boron ate-complex with a rigid diamantane geometry. 3N-TAADs bearing N-acyl and alkoxycarbonyl groups form guest–host complexes with water or methanol, in which the guest

Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• the 1,6-enyne 35 followed by reductive elimination of the carbon nucleophile 38. Interestingly, this reaction proceeds via the cleavage of heteroelements and activated C–C bonds prior to reductive elimination of the metallacyclic ate-complex, resulting in the net formation of two new C–C bonds

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

• Cécile Verrier,
• Pierrik Lassalas,
• Laure Théveau,
• Guy Quéguiner,
• François Trécourt,
• Francis Marsais and
• Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

• in this article. Methodologies, selectivity, mechanism and future aspects are presented. Keywords: ate complex; catalytic direct arylation; mechanism; oxazole; selectivity; transition-metal catalysis; Introduction Deprotonative metalation of aromatics is widely used as a powerful method for

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

• Benito Alcaide and
• Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73

• 32. The elimination of methoxymethanol followed by isomerization would lead to the metallaoxocarbenium species 33. Subsequent nucleophilic attack by water, from trace amounts present in the solvent or the catalyst, from the less hindered face of intermediate 33 would form the ate complex 34

Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts

• Hélio A. Stefani,
• Rafael C. Guadagnin,
• Artur F. Keppler,
• Giancarlo V. Botteselle,
• João V. Comasseto and
• Carlos A. Suganuma

Beilstein J. Org. Chem. 2008, 4, No. 9, doi:10.1186/1860-5397-4-9

• ), generates nBu•, which is responsible for the cis-trans isomerization. The butyl radical attack occurs at the boronic “ate” complex 4 (Scheme 1) [16], yielding the nBuBF3K salt as a final product. In order to verify the presence of radical species in the reaction mixture, we performed EPR spin trapping

• homolytic cleavage of the nBu-Te bond of the compound 3, caused by the lithium species present in the reaction medium. The second step consists of an attack of 5 at the boronic “ate” complex 4, leading to the vinylic radical, which undergoes self-isomerization to the most stable isomer 8. In the third step

• the coupling constants of the vinylic hydrogens for each intermediate of the reaction route. Using this approach, we could prove the cis geometry of the vinylic hydrogens of the intermediate 2 (Scheme 1), which presented a coupling constant of 18.09 Hz [14][15]. Unfortunately, the boronic “ate