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

• -iodo-4-perfluorohexylthiophene, which was separated by column chromatography. Compound 4 then underwent Suzuki–Miyaura coupling with compound 5, which was synthesised according to our previously published method [17], and the product obtained, 6, was deprotected by bromination to give compound 7 and

Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach

• Sandeep Kumar,
• Ramendra Pratap,
• Abhinav Kumar,
• Brijesh Kumar,
• Vishnu K. Tandon and
• Vishnu Ji Ram

Beilstein J. Org. Chem. 2013, 9, 809–817, doi:10.3762/bjoc.9.92

• hydride-AIBN initiated radical cyclization [33][34]. In 2005, Player and co-workers reported a tandem Heck/Suzuki–Miyaura coupling process for the synthesis of (E)-3,3-(diaryl)oxindoles [35][36][37]. Recently, alkenylation of indolin-2-ones has been developed by palladium-catalyzed aromatic C–H activation

Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

• Jeelani Basha Shaik,
• Venkatachalam Ramkumar,
• Babu Varghese and
• Sethuraman Sankararaman

Beilstein J. Org. Chem. 2013, 9, 698–704, doi:10.3762/bjoc.9.79

• Abstract trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki–Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and

• structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl-1,2,3-triazol-5-ylidene as the ligand. Keywords: C–C coupling; N-heterocyclic carbene; palladium; Suzuki–Miyaura coupling; 1,2,3

• reactions one often encounters the formation of partially coupled products and incomplete reactions leading to problematic separation of pure fully substituted compounds. Herein we report very clean multiple Suzuki–Miyaura coupling of polybromoarenes. In every case reported herein the final product, namely

Extending the utility of [Pd(NHC)(cinnamyl)Cl] precatalysts: Direct arylation of heterocycles

• Anthony R. Martin,
• Anthony Chartoire,
• Alexandra M. Z. Slawin and
• Steven P. Nolan

Beilstein J. Org. Chem. 2012, 8, 1637–1643, doi:10.3762/bjoc.8.187

• ) (Figure 1). Complexes 1 and 2 are commercially available and have proven to be highly efficient in Suzuki–Miyaura coupling and Buchwald–Hartwig amination reactions [17][18][19][20]. We have also evaluated the recently reported [Pd(IPr*)(cin)Cl] (3), which has shown potency in Suzuki–Miyaura couplings [21

Sonogashira–Hagihara reactions of halogenated glycals

• Dennis C. Koester and
• Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

• Suzuki–Miyaura coupling with iodoglucals 6 to yield aliphatic C-glycosides [19]. This method impressively demonstrates the power of the Suzuki–Miyaura coupling in the formation of C(sp2)–C(sp3) bonds for the preparation of carbohydrate mimetics. Friesen and co-workers reported on a synthesis of aryl-C

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• of 7a and 7b in modest yields (40% and 20%, respectively). Sexithiophenes 1a and 1b were subsequently isolated following Suzuki–Miyaura coupling with 4-(dimethylamino)phenylboronic acid (1a, 28%; 1b, 44%). As a comparison, nonfunctionalised sexithiophenes 2a and 2b were also synthesised in order to

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• stereoselectivity. A four-component reaction was further developed through an in situ post C–B arylation by adding a second aryl iodide, with Cs2CO3 and water, to the newly formed alkenylboronate 78. The subsequent Suzuki–Miyaura coupling led to the formation of 2,3-diarylated amines 79 and the best results were

Bromine–lithium exchange: An efficient tool in the modular construction of biaryl ligands

• Laurence Bonnafoux,
• Frédéric R. Leroux and
• Françoise Colobert

Beilstein J. Org. Chem. 2011, 7, 1278–1287, doi:10.3762/bjoc.7.148

• -methylation with iodomethane in acetone. 2,2'-Dibromo-6-methoxybiphenyl (1d) was finally obtained in a very good global yield of 68% in 3 steps. Finally, we proposed to introduce the phenyl ring (1f, 95%) by a regioselective Suzuki–Miyaura coupling via the iodo derivative 1e, the latter being obtained in 83

Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis

• Lian-jun Liu,
• Feijun Wang,
• Wenfeng Wang,
• Mei-xin Zhao and
• Min Shi

Beilstein J. Org. Chem. 2011, 7, 555–564, doi:10.3762/bjoc.7.64

• ][64][65][66]. NHC–Allylpalladium complexes have been employed and showed good catalytic activities in carbon–carbon bond coupling reactions [67][68][69][70]. Stereoisomeric complex 7 was firstly applied as the catalyst in the catalyze Suzuki–Miyaura coupling reaction. On the basis of screening of the

Air-stable, recyclable, and time-efficient diphenylphosphinite cellulose-supported palladium nanoparticles as a catalyst for Suzuki–Miyaura reactions

• Qingwei Du and
• Yiqun Li

Beilstein J. Org. Chem. 2011, 7, 378–385, doi:10.3762/bjoc.7.48

• . Moreover, it showed excellent catalytic activity in the Suzuki–Miyaura coupling reaction of various aryl haildes bearing electron-withdrawing and/or electron-donating groups. Results and Discussion Synthesis and characterization of Cell–OPPh2 and Cell–OPPh2–Pd0 It is well known that nanopalladium shows

Syntheses and properties of thienyl-substituted dithienophenazines

• Annemarie Meyer,
• Eva Sigmund,
• Friedhelm Luppertz,
• Gregor Schnakenburg,
• Immanuel Gadaczek,
• Thomas Bredow,
• Stefan-S. Jester and
• Sigurd Höger

Beilstein J. Org. Chem. 2010, 6, 1180–1187, doi:10.3762/bjoc.6.135

• quantitative yield [21][22]. The respective regio isomer 8 was synthesized starting from commercially available 3-bromothiophene 1 and boronic acid 5 in three steps (Scheme 2). By Suzuki–Miyaura coupling we obtained 3,3’-bithiophene in good yields. The red diketone 7 was prepared by two-fold acylation with

Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst

• Guangming Nan,
• Fang Ren and
• Meiming Luo

Beilstein J. Org. Chem. 2010, 6, No. 70, doi:10.3762/bjoc.6.70

• development of a recyclable catalytic system for the Suzuki–Miyaura coupling reactions of 1-aryltriazenes is highly desirable. Although several types of heterogenous catalytic systems have been described for the Suzuki–Miyaura reactions of aryl halides [30], to the best of our knowledge, there has been no

Solvent-free and time-efficient Suzuki–Miyaura reaction in a ball mill: the solid reagent system KF–Al₂O₃ under inspection

• Franziska Bernhardt,
• Ronald Trotzki,
• Tony Szuppa,
• Achim Stolle and
• Bernd Ondruschka

Beilstein J. Org. Chem. 2010, 6, No. 7, doi:10.3762/bjoc.6.7

• pH measurements of aqueous suspension of the pure aluminas. Investigating the influence of different SRS, the Pd(OAc)2-assisted Suzuki–Miyaura coupling of phenylboronic acid (1) with different aryl bromides 2 furnishing p-substituted biphenyls 3 (Scheme 1) was chosen. Reactions were performed in a

• couplings applying ball milling conditions [55][56], respectively, the reaction times were substantially reduced from several hours to a few minutes following the present reaction protocol. A comparison of the results from the Suzuki–Miyaura coupling of 1 with p-bromoacetophenone (2a) assisted by pure

• -loaded aluminas as basic solid reagent systems (SRS) for the solvent free Suzuki–Miyaura coupling of aryl bromides with phenylboronic acid induced by ball milling was investigated. Coupling experiments with unloaded aluminas revealed that reactivity follows the inverse basicity of KF free SRS applied for