N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions

• Senem Akkoç,
• Yetkin Gök,
• İlhan Özer İlhan and
• Veysel Kayser

Beilstein J. Org. Chem. 2016, 12, 81–88, doi:10.3762/bjoc.12.9

• with 4-chlorotoluene. Keywords: arylation; benzimidazolium salts; catalysis; N-heterocyclic carbene; PEPPSI complex; Suzuki–Miyaura cross-coupling reaction; Introduction The use of N-heterocyclic carbenes (NHCs) as ligands was started by Wanzlick [1] and Öfele [2] almost fifty years ago. There have

• compounds in Suzuki–Miyaura cross-coupling reaction The Suzuki–Miyaura cross-coupling reaction, which has mostly been performed in organic solvents until recently, can now be performed using green solvents under mild conditions [29][30][31][32][33][34]. We used H2O with DMF as solvents in different

• bromidesa,b. Suzuki–Miyaura cross-coupling reaction of phenylboronic acid with aryl chloridesa,b. Suzuki–Miyaura cross-coupling reaction of boronic acid derivatives with aryl halidesa,b. Suzuki–Miyaura cross-coupling reaction of boronic acid derivatives with aryl chloridesa,b. Supporting Information

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

• Tatjana Huber,
• Lara Weisheit and
• Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

• -membered carbocycle was realized via a B-alkyl Suzuki–Miyaura cross-coupling reaction. Optimization studies of this key ring closure with different protecting groups on the lactol functionality revealed methyl acetal 135 as the most efficient substrate for this transformation. The challenging key step was

The simple production of nonsymmetric quaterpyridines through Kröhnke pyridine synthesis

• Isabelle Sasaki,
• Jean-Claude Daran and
• Gérard Commenges

Beilstein J. Org. Chem. 2015, 11, 1781–1785, doi:10.3762/bjoc.11.193

• pathway [17][20], or a Suzuki–Miyaura cross-coupling reaction [21]. The use of triazine derivatives (which under particular conditions undergo an inverse Diels–Alder reaction) can also produce oligopyridines [22]. On the other hand, there are a limited number of reports dealing with the preparation of

Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki–Miyaura reactions: relative reactivity of K[4-RC₆F₄BF₃] and the role of silver-assistance in acceleration of transmetallation

• Vadim V. Bardin,
• Anton Yu. Shabalin and
• Nicolay Yu. Adonin

Beilstein J. Org. Chem. 2015, 11, 608–616, doi:10.3762/bjoc.11.68

• continuation of systematic research of the Suzuki–Miyaura cross-coupling reaction of weakly nucleophilic organotrifluoroborates we report here the study of the relative reactivity of K[4-RC6F4BF3] in the Pd-catalyzed reactions with some aryl bromides and iodides in the presence of Ag2O. The borates were chosen

Aryl substitution of pentacenes

• Andreas R. Waterloo,
• Anna-Chiara Sale,
• Dan Lehnherr,
• Frank Hampel and
• Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

• nucleophilic addition (yields given are for the pentacene product 3, over the two steps from either 4a or 4b). Functionalization of iodoaryl pentacene 3g using the Suzuki–Miyaura cross-coupling reaction. Optical properties of pentacenes 3a–k, unsubstituted pentacene (PEN), and TIPSPc. Thermal properties of a

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

• reaction produced the arylstannane in 75 to 90% yield [88]. The Suzuki–Miyaura cross-coupling reaction is another type of reaction with the phosphate group acting as a leaving group. As exemplified in Scheme 30, the aryl dialkyl phosphate was produced in good yield by an AT reaction [89]. Then, this

Palladium-catalysed cross-coupling reaction of ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole compounds with aryl bromides: A direct protocol for the preparation of unsymmetrical biaryls

• Siphamandla Sithebe and
• Ross S. Robinson

Beilstein J. Org. Chem. 2014, 10, 1107–1113, doi:10.3762/bjoc.10.109

• absorption and fluorescence characteristics. Here we describe the first palladium-catalysed Suzuki–Miyaura cross-coupling reaction of easily accessible and ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole derivatives with various aryl bromides. Aryl bromides bearing electron-withdrawing

• [1][2][3][4][5]. Amongst them, the Suzuki–Miyaura cross-coupling reaction of aryl halides/triflates and organoboron compounds is one of the most documented and versatile cross-coupling reaction in the literature [6]. The use of organoboron compounds 1, 2 and 3 (Figure 1) as nucleophilic coupling

• partners in the Suzuki–Miyaura cross-coupling reaction is particularly attractive due to the non-toxicity of the byproducts, the ease with which they are transmetalated and their high stability towards air and moisture, which are the key features for coupling reactions [7]. On one hand, structural diverse

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

• Affording valued biaryls and heterobiaryls, namely ubiquitous chemical moieties in pharmaceuticals, natural products, photoactive species and many other functional molecules, the Suzuki–Miyaura cross-coupling reaction is widely employed by the fine chemicals and pharmaceutical industries [1]. The reaction

Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties

• Binod Babu Shrestha,
• Shuhei Higashibayashi and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2014, 10, 841–847, doi:10.3762/bjoc.10.80

• Pyrenylsumanene (1) was prepared from iodosumanene [8] and pyreneboronic acid in 84% yield through a Suzuki–Miyaura cross-coupling reaction (Scheme 1). The preparation of iodosumanene was improved by using a catalytic amount of scandium (III)triflate (Sc(OTf)3) with 6,6’-diiodo-2,2’-dimethoxy-1,1’-binaphthol (DIH

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

• diphenylphosphinite cellulose-supported nanopalladium catalyst, it was initially used in the Suzuki–Miyaura cross-coupling reaction, which is a versatile and a well studied method for the generation of Csp2–Csp2 bonds in organic synthesis. The influence of base, solvent and amount of catalyst on Suzuki–Miyaura cross

• –Pd0). General procedure for the Suzuki–Miyaura cross-coupling reaction In a typical experiment, the Cell–OPPh2–Pd0 catalyst (0.005 mmol of Pd) was added to a mixture of aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), and K2CO3 (2.0 mmol) in 95% ethanol (5 cm3), and the reaction mixture was

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

• Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported Pd–NHC complex catalyst has been realized for the first time. The polymer-supported catalyst can be re-used several times still retaining high activity for this transformation

• electrophilic component [5][6][7][8][9][10][11][12][13][14][15][16][17][18]. As an additional candidate for the electrophilic coupling partner, arenediazonium salts have also been used in place of aryl halides in the Suzuki–Miyaura cross-coupling reaction, and show higher activity than the corresponding aryl

• arenediazonium salt surrogates in the Suzuki–Miyaura cross-coupling reaction [29]. Pd2(dba)3 and P(tBu)3 were used as catalyst in this reaction where, as in most of homogeneous catalytic systems, the difficulties of catalyst recovery and recycling constitute major problems. One possible solution to these

Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines

• Susan Kelleher,
• Pierre-Yves Quesne and
• Paul Evans

Beilstein J. Org. Chem. 2009, 5, No. 69, doi:10.3762/bjoc.5.69

• above proving inefficient, palladium chemistry was subsequently considered. The vinyl bromide 24a was reported to participate in Sonagashira alkynylation chemistry; however, yields of the resultant enyne were low [20]. Therefore, we decided to investigate Suzuki–Miyaura cross-coupling reaction as a