Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• was observed (86.5:13.5 to 89:11 er). Luo and Cheng also explored the mechanism of the Friedel–Crafts addition of indole to α-substituted vinyl ketones [52][53]. Based on DFT studies, the authors proposed that the stereoselectivity of the reaction was under Curtin–Hammett control (Scheme 28). During

Recent advances in C(sp³)–H bond functionalization via metal–carbene insertions

• Bo Wang,
• Di Qiu,
• Yan Zhang and
• Jianbo Wang

Beilstein J. Org. Chem. 2016, 12, 796–804, doi:10.3762/bjoc.12.78

• metal center to the ligand and to carbon dioxide was supported by experimental data and DFT studies. Such interaction increases the electrophilicity of the carbene moiety and thus lowers the activation energy for C–H bond insertion. Other ligands have also been explored for the metal–carbene C(sp3)–H

• except for methane (Scheme 11). The DFT studies suggested that formation of the silver carbene complex was the rate-determining step for alkane substrates such as ethane and propane. As for methane, the overall rate-determining step was carbene insertion into the C–H bond, attributed to the inertness of

Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products

• Sultan Taskaya,
• Nurettin Menges and
• Metin Balci

Beilstein J. Org. Chem. 2015, 11, 897–905, doi:10.3762/bjoc.11.101

• -one derivatives. Some of the exo-cyclic double bonds underwent isomerization to endo-cyclic compounds upon treatment with TFA, while some did not. DFT studies supported our findings. Moreover, cyclization reactions in the presence of alcohol formed hemiacetal derivatives after gold-catalyzed cascade

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

On the control of secondary carbanion structure utilising ligand effects during directed metallation

• Andrew E. H. Wheatley,
• Jonathan Clayden,
• Ian H. Hillier,
• Alison Campbell Smith,
• Mark A. Vincent,
• Laurence J. Taylor and
• Joanna Haywood

Beilstein J. Org. Chem. 2012, 8, 50–60, doi:10.3762/bjoc.8.5

• presence of different Lewis bases. In contrast to previous work on carbanion formation in the presence of an aromatic N+O directing group, 6-Lil·L dissolves in hydrocarbon media to reveal two structures in solution. Based on previous work and new DFT studies, we ascribe these as being cis (minor) and trans

Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation

• David R. Armstrong,
• Liam Balloch,
• Eva Hevia,
• Alan R. Kennedy,
• Robert E. Mulvey,
• Charles T. O'Hara and
• Stuart D. Robertson

Beilstein J. Org. Chem. 2011, 7, 1234–1248, doi:10.3762/bjoc.7.144

• crystallographically characterised starting materials and the thermodynamic final products, Uchiyama and Nobuto have studied and evaluated the possible reaction pathways of the deprotonative metallation of benzene with sodium TMP-zincate 1 computationally [26]. Their DFT studies propose that these distinctive

• synergic base, and the harsh reflux conditions required to bring about the presence of the meta-zincated derivative offers less control, ultimately leading to competing di-metallation of the aromatic substrate. In addition DFT studies probing the different metallation regioselectivities obtained from

SbCl₃-catalyzed one-pot synthesis of 4,4′-diaminotriarylmethanes under solvent-free conditions: Synthesis, characterization, and DFT studies

• Ghasem Rezanejade Bardajee

Beilstein J. Org. Chem. 2011, 7, 135–144, doi:10.3762/bjoc.7.19