Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• functionalizing poorly soluble compounds, functionalized HBC is typically synthesized by dehydrogenative cyclization, which is called Scholl reaction, of precursors having solubilizing substituents [12][13]. However, the Scholl reaction sometimes causes unexpected rearrangement such as 1,2-aryl shift, and

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• . Moreover, they found that this fluorination also proceeds with catalytic amounts of the iodoarenes in the presence of mCPBA as a terminal oxidant, albeit in lower yields (Scheme 15) [67]. Mechanistically, the 1,2-aryl shift could arise via phenonium intermediates 49 to deliver the geminal difluorination

Some aspects of radical chemistry in the assembly of complex molecular architectures

• Béatrice Quiclet-Sire and
• Samir Z. Zard

Beilstein J. Org. Chem. 2013, 9, 557–576, doi:10.3762/bjoc.9.61

• -arylpiperidines. This strategy is illuminated by the synthetic outline in Scheme 24, where the intermediate radical 124 arising from addition to alkene 123 undergoes a 1,2-aryl shift via cyclopropane 125, a process made irreversible by elimination of a methylsulfonyl radical to give ester 126 [52]. Two new C–C

Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

• Paul W. Davies,
• Nicolas Martin and
• Neil Spencer

Beilstein J. Org. Chem. 2011, 7, 839–846, doi:10.3762/bjoc.7.96

• Paul W. Davies Nicolas Martin Neil Spencer School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, United Kingdom 10.3762/bjoc.7.96 Abstract Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl

• - and deuterium-labelled substrates. Keywords: 1,2-aryl shift; cycloisomerisation; gold; isotopic labelling; pyrrole; skeletal rearrangement; Introduction Gold-catalysed cycloisomerisation reactions have emerged as powerful methods to construct a diverse array of hetero- and carbocyclic motifs under

• through Path II, where a 1,2-aryl shift (B→E) precedes proton elimination (E→F) and protodemetallation. The observed solvent and counter ion effects could be rationalised by considering that the 1,2-aryl shift at B is disfavoured relative to proton elimination as its cationic character is diminished