Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

• Togni’s reagent [87]. On the other hand, K. J Szabó et al. had to use stoichiometric amounts of copper(I) cyanide and catalytic bis(pinacolato)diboron to achieve optimal yields, but a catalytic amount of CuCN could also produce the desired trifluoromethylated products if stoichiometric potassium or

• interest of this reaction resides in the fact that the Ir-catalyzed borylation with bis(pinacolato)diboron is highly influenced by the steric bulk of the arene, and therefore leads to regioselective functionalization of the substrate. Arenes and heteroarenes, variously substituted, could undergo the

Incorporation of perfluorohexyl-functionalised thiophenes into oligofluorene-truxenes: synthesis and physical properties

• Neil Thomson,
• Alexander L. Kanibolotsky,
• Joseph Cameron,
• Tell Tuttle,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2013, 9, 1243–1251, doi:10.3762/bjoc.9.141

• then reacted with bis(pinacolato)diboron to afford boronic ester 8. The synthetic route to 2-iodo-4-perfluorohexylthiophene (13) (Scheme 2) began with treatment of 3-bromothiophene (1) with lithium bis(trimethylsilyl)amide and chlorotrimethylsilane to afford 2-trimethylsilyl-3-bromothiophene (9

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

• Sarah L. Harding,
• Sebastian M. Marcuccio and
• G. Paul Savage

Beilstein J. Org. Chem. 2012, 8, 606–612, doi:10.3762/bjoc.8.67

• also undergo many of these coupling reactions and Miyaura’s protocol for the palladium-catalysed cross-coupling of bis(pinacolato)diboron with aryl and vinyl halides or triflates has become one of the most popular methods for preparing arylboronic esters under mild conditions [11]. The resulting

Convenient methods for preparing π-conjugated linkers as building blocks for modular chemistry

• Jiří Kulhánek,
• Filip Bureš and
• Miroslav Ludwig

Beilstein J. Org. Chem. 2009, 5, No. 11, doi:10.3762/bjoc.5.11

• the Horner–Wadsworth–Emmons reaction described above. These substituted 4-bromostilbenes could be most effectively converted to target pinacol esters 5a–c via borylation (Scheme 1, Method C) utilizing bis(pinacolato)diboron (pin2B2) [39] in a mixed solvent system DMSO/dioxane ensuring good solubility

• . Overall 12 extended π-linkers have been easily synthesized (8 of them are new compounds) utilizing procedures such as a lithiation/reaction with triisopropyl borate/esterification with pinacol, Mizoroki–Heck coupling with vinylboronate pinacol ester, borylation with bis(pinacolato)diboron or Sonogashira