Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

• H. Surya Prakash Rao and
• A. Veera Bhadra Rao

Beilstein J. Org. Chem. 2016, 12, 496–504, doi:10.3762/bjoc.12.49

• preparation of the starting diarylmethanol 20, which was accomplished by the addition the anion from 9-bromophenanthrene [63] 19 to 4-methoxybenzaldehdye. The resulting diarylmethanol 20 was treated with bis(pinacolato)diboron [64] 10n, which has an 2-nitrobenzyl protecting group on the phenolic hydroxy group

Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water

• Lei Zhu,
• Taku Kitanosono,
• Pengyu Xu and
• Shū Kobayashi

Beilstein J. Org. Chem. 2015, 11, 2007–2011, doi:10.3762/bjoc.11.217

• chiral 2,2′-bipyridine ligand L for 1 h. After successive addition of cinnamonitrile (1a) and bis(pinacolato)diboron, the resulting mixture was stirred at room temperature for 12 h. Subsequent oxidation by treatment with NaBO3 was conducted to determine the enantioselectivity. The desired β

Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

• Katherine M. Byrd

Beilstein J. Org. Chem. 2015, 11, 530–562, doi:10.3762/bjoc.11.60

• and least toxic choice. Though there are many examples of copper-catalyzed 1,4-additions of boron, most of the reports use bis(pinacolato)diboron (B2pin2) as a source of boron. In 2013, Molander and co-workers reported the asymmetric 1,4-addition of bisboronic acid (BBA) and tetrakis(dimethylamino

Clean and fast cross-coupling of aryl halides in one-pot

• Valerica Pandarus,
• Geneviève Gingras,
• François Béland,
• Rosaria Ciriminna and
• Mario Pagliaro

Beilstein J. Org. Chem. 2014, 10, 897–901, doi:10.3762/bjoc.10.87

• Unsymmetrically coupled biaryls are synthesized in high yield starting from different aryl bromides and bis(pinacolato)diboron by carrying out the Miyaura borylation reaction followed by the Suzuki–Miyaura reaction in the same reaction pot over 1–2 mol % SiliaCat DPP-Pd. The SiliaCat DPP-Pd catalyst is air-stable

• following Miyaura’s discovery from 1995. He demonstrated a direct route to boronic esters [2], namely the cross-coupling of bis(pinacolato)diboron (B2Pin2) with aryl or vinyl halides catalyzed by PdCl2(dppf) ([1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride) in the presence of excess KOAc at

• emerging as a promising tool for synthetic organic chemistry [9]. In this research context, we have recently described the heterogeneously catalyzed synthesis of boronic acid pinacol esters using a wide range of aryl chlorides, bromides and iodides and bis(pinacolato)diboron as borylating agent over the

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