Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

• Carlos R. Azpilcueta-Nicolas and
• Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

• decarboxylative cross-coupling (DCC) of NHPI esters with organometallic reagents, resembling classic Kumada, Negishi, and Suzuki couplings, has been enabled by nickel (Ni), cobalt (Co), iron (Fe), and copper (Cu) catalysts [84][85][86][87][88][89][90][91] (Scheme 23A). The typical mechanism begins by

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

• Vânia F. Pais,
• Tristan Neumann,
• Ignacio Vayá,
• M. Consuelo Jiménez,
• Abel Ros and
• Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

• , 41012 Seville, Spain 10.3762/bjoc.15.254 Abstract Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki

• couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

• Arne Klinkebiel,
• Ole Beyer,
• Barbara Malawko and
• Ulrich Lüning

Beilstein J. Org. Chem. 2016, 12, 2267–2273, doi:10.3762/bjoc.12.219

• resulting in the formation of the desired triazines 3b and 3c in 53 and 61% yield, respectively. Following the synthetic plan of Figure 3, the tribromides 3b and 3c were used in the Suzuki couplings. In this and respective following synthetic steps, optimization of the reaction conditions was very important

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112

• the corresponding N-oxide 8. Suzuki-couplings of 2,2'-bipyrid-4-yl nonaflates 5a and 5b to compounds 9 and 10. Palladium-catalyzed couplings of chloro-substituted 2,2'-bipyrid-4-yl nonaflate 5g leading to compounds 11, 12 and 13. Attempted TMSOTf/DIPEA-promoted cyclocondensations of β-ketoenamides 3a

Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

• Ludovic Eberlin,
• Fabien Tripoteau,
• François Carreaux,
• Andrew Whiting and
• Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

• tools in synthetic organic chemistry. The most significant recent results and developments obtained in this area are reported in this review. Keywords: allylboration; boron compounds; Diels–Alder; 1,3-dienes; multicomponent reactions; Petasis borono–Mannich; Suzuki couplings; Introduction

Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

• Kalicharan Chattopadhyay,
• Erik Fenster,
• Alexander J. Grenning and
• Jon A. Tunge

Beilstein J. Org. Chem. 2012, 8, 1200–1207, doi:10.3762/bjoc.8.133

• tolerated on the coumarin core. In addition to the above Suzuki couplings, acetoxymethylcoumarins were found to undergo palladium-catalyzed substitution with sulfinates and secondary amines under the previously developed palladium-catalysis conditions (Scheme 4). Importantly, related aminomethylcoumarins

On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch

• Virginia Mazzanti,
• Martina Cacciarini,
• Søren L. Broman,
• Christian R. Parker,
• Magnus Schau-Magnussen,
• Andrew D. Bond and
• Mogens B. Nielsen

Beilstein J. Org. Chem. 2012, 8, 958–966, doi:10.3762/bjoc.8.108

• Suzuki couplings (as previously accomplished for the 7-bromo-substituted DHA) have so far been unsuccessful. It seems that the 3-bromo functionality is not very reactive, which is reflected as well by the regioselective Sonogashira and Suzuki reactions on the 3,7-dibromoazulene 14 reported in this work

• functionalization of DHA [3][5][6][7][8]. HMDS = hexamethyldisilazide. Bromination of VHF [11]. NBS = N-bromosuccinimide. Radical and ionic brominations of VHF. Synthesis of 3,7-dibromo-DHA. Synthesis of a 3,7-dibromoazulene. Regioselective Sonogashira and Suzuki couplings. RuPhos = 2-dicyclohexylphosphino-2',6

Double N-arylation reaction of polyhalogenated 4,4’-bipyridines. Expedious synthesis of functionalized 2,7-diazacarbazoles

• Mohamed Abboud,
• Emmanuel Aubert and
• Victor Mamane

Beilstein J. Org. Chem. 2012, 8, 253–258, doi:10.3762/bjoc.8.26

• system. Moderate to good yields were obtained in this site-selective Buchwald–Hartwig double amination. The functionalization of these tricyclic derivatives was performed by using Pd-catalyzed cross-coupling reactions such as the Stille and Suzuki couplings. Two compounds were analyzed by X-ray

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• -containing polymers are considerably more stable than the DPP monomers or non-conjugated DPP-polymers. Dehaen et al. used a stepwise sequence of Suzuki couplings to prepare rod-like DPP-phenylene oligomers with well-defined lengths [26]. The resulting oligomers contained three, five and seven DPP units

Palladium- catalyzed cross coupling reactions of 4-bromo- 6H-1,2-oxazines

• Reinhold Zimmer,
• Elmar Schmidt,
• Michal Andrä,
• Marcel-Antoine Duhs,
• Igor Linder and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2009, 5, No. 44, doi:10.3762/bjoc.5.44

• . C17H21NO2Si (299.5): calcd. C, 68.19; H, 7.07; N, 4.68; found: C, 68.17; H, 7.08; N, 4.74. Brominations of 6H-1,2-oxazines. a) Br2, Et2O, −30 °C, 2 h. b) Et3N, −30 °C to r.t., overnight. Chlorinations of 6H-1,2-oxazines. a) Cl2, Et2O, −30 °C. b) Et3N, −30 °C to r.t. Suzuki-couplings of 4-bromo-6H-1,2-oxazines

Polyionic polymers – heterogeneous media for metal nanoparticles as catalyst in Suzuki–Miyaura and Heck–Mizoroki reactions under flow conditions

• Klaas Mennecke and
• Andreas Kirschning

Beilstein J. Org. Chem. 2009, 5, No. 21, doi:10.3762/bjoc.5.21

• sources for soluble, catalytically active species during the course of Heck and Suzuki couplings. They note a solution-phase contribution for catalysis and determined leaching up to 46% in DMF as solvent which is significantly higher compared to our polyionic gels: Broadwater, S. J.; McQuade, D. T. J

A convenient catalyst system for microwave accelerated cross- coupling of a range of aryl boronic acids with aryl chlorides

• Matthew L. Clarke,
• Marcia B. France,
• Jose A. Fuentes,
• Edward J. Milton and
• Geoffrey J. Roff

Beilstein J. Org. Chem. 2007, 3, No. 18, doi:10.1186/1860-5397-3-18

• conditions yields only 1,2,5 trifluorobenzene as the only fluorine containing product. Protodeboronation is therefore the cause of the low reactivity observed here, and is a likely problem in other Suzuki couplings of highly fluorinated substrates. Finally, we stirred 2,3,6-trifluorophenyl boronic acid with

• be obtained in 15 minutes or less. Heavily fluorinated boronic acids do not participate in these Suzuki couplings due to protodeboronation. The accessibility, low cost of the catalyst, short reactions times and convenience of these procedures should make them useful in small scale biaryl synthesis