Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives

• Fatma Belkessam,
• Aidene Mohand,
• Jean-François Soulé,
• Abdelhamid Elias and
• Henri Doucet

Beilstein J. Org. Chem. 2014, 10, 2912–2919, doi:10.3762/bjoc.10.309

• semiconductors [2]. Due to these multiple uses, the discovery of a simpler access to terthiophene derivatives would be very useful. Suzuki, Stille or Negishi Pd-catalyzed cross-coupling reactions represent some of the most efficient methods for the preparation of 2,5-diheteroarylated thiophenes [3][4][5][6][7][8

• than other Pd-catalyzed cross-coupling reactions as it avoids the preparation of an organometallic derivative and also as the major byproducts of the reaction are not metallic salts but a base associated to HX. The metal-catalyzed direct arylation of a wide variety of heteroarenes using aryl halides as

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

• opportunity to vary the pendent substituent through a Pd-catalyzed cross-coupling protocol (Scheme 2). Thus, pentacene 3g was treated under Suzuki–Miyaura coupling conditions with arylboronic acids, and the desired pentacenes 3j,k were obtained in yields of 92 and 68%, respectively. Notably, anthracenyl

Preparation of phosphines through C–P bond formation

• Iris Wauters,
• Wouter Debrouwer and
• Christian V. Stevens

Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106

Iron-containing mesoporous aluminosilicate catalyzed direct alkenylation of phenols: Facile synthesis of 1,1-diarylalkenes

• Satyajit Haldar and
• Subratanath Koner

Beilstein J. Org. Chem. 2013, 9, 49–55, doi:10.3762/bjoc.9.6

• the literature that involve Pd-catalyzed cross coupling reactions of various aryl halides with different olefins. However, the major drawback of the Mizoroki–Heck-type reaction in the synthesis of 1,1-disubstituted olefins rests on its poor selectivity toward the formation of α-products [20][21][22

Diarylethene-modified nucleotides for switching optical properties in DNA

• Sebastian Barrois and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2012, 8, 905–914, doi:10.3762/bjoc.8.103

• , forms the central cyclopentane ring of diarylethene 10. Subsequently, the ethynyl linker is attached to 10 by treatment with TMS-protected acetylene in a Pd-catalyzed cross-coupling reaction. Careful evaluation of this synthetic step revealed that the best yield (43%) of the mono-ethinylated product 11

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

• glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a

• the use of these compounds in the synthesis of aryl-, allyl- and benzyl-C-glycosides [16]. The group of Minehan described another fascinating approach to aryl-C-glycosides in 2003 [17]. They showed that aryl-C-glycosides can be prepared from glycalyl indium(III) compounds (e.g., 4) in a Pd-catalyzed

• cross-coupling reaction with iodoarenes. However, it is not only metalated sugar derivatives that have prevailed in the synthesis of C-glycosides, but also some electrophilic coupling reagents, such as glycalyl phosphates, and bromo- and iodoglycals. Glycal phosphates of type 5 were employed as

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

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

• Pd-catalyzed cross-coupling approach starting from 1-chloro-2-iodobenzenes, phenylacetylene and a variety of primary amines [28][29]. The sequential three-component reaction was performed with the aid of an N-heterocyclic carbene-palladium complex generated in situ, derived from imidazolium salt 50

Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

• Inhee Cho,
• Labros Meimetis,
• Lee Belding,
• Michael J. Katz,
• Travis Dudding and
• Robert Britton

Beilstein J. Org. Chem. 2011, 7, 1315–1322, doi:10.3762/bjoc.7.154

• derivatives through Pd-catalyzed cross-coupling reactions (Scheme 5). This approach compliments those described above and avoids the need to protect the diol function prior to the cross-coupling step. Notably, purification of the bis(benzoxaborol) 20 proved unnecessary as the diphenylhydrobenzoin 34 was

• Pd-catalyzed cross-coupling of the known triflate 35 [35] with the bis(benzoxaborol) 20 afforded the dicyclooctenylhydrobenzoin 36, which was reduced in quantitative yield to afford Vivol (4) by Hall [3]. Notably, this three-step procedure for the preparation of optically pure Vivol compares well

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

• Paul Knochel,
• Matthias A. Schade,
• Sebastian Bernhardt,
• Georg Manolikakes,
• Albrecht Metzger,
• Fabian M. Piller,
• Christoph J. Rohbogner and
• Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

• the most important procedures for the preparation of functionalized organzinc and organomagnesium reagents. In addition, new methods for the preparation of polyfunctional aryl- and heteroaryl zinc- and magnesium compounds, as well as new Pd-catalyzed cross-coupling reactions, are reported herein

• pharmaceutical research. In this review article, we describe the approaches to this problem that use functionalized magnesium and zinc heterocyclic intermediates. Some typical experimental procedures are indicated in each case for the most important methods. New Pd-catalyzed cross-coupling procedures are also

• readily converted to the desired zinc reagents 31. The Pd-catalyzed cross-coupling of 31 with the iodoquinoline 32 and with S-Phos as ligand [15][16][17] provides the alkaloid papaverine (33) in 68% yield (Scheme 5) [13]. Ni-catalyzed cross-couplings can also be realized [14]. Thus, the reaction of the

Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans

• Verónica Guilarte,
• M. Pilar Castroviejo,
• Estela Álvarez and
• Roberto Sanz

Beilstein J. Org. Chem. 2011, 7, 1255–1260, doi:10.3762/bjoc.7.146

• 2,3-difunctionalized phenol derivatives were applied to the synthesis of 4-functionalized benzo[b]furans [39], 4- or 7-alkoxyindoles [40], and 7-oxy-substituted benzo[b]thiophenes [41] by employing Pd-catalyzed cross-coupling reactions or halocyclization processes. Following our interest in the

One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation–decarbonylative alkynylation–cyclocondensation sequences

• Charlotte F. Gers,
• Julia Rosellen,
• Eugen Merkul and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1173–1181, doi:10.3762/bjoc.7.136

• chemistry has recently been reported [39]. N-Heteroaryl-substituted azulenes can be accessed by stoichiometric [40][41] as well as Pd-catalyzed cross-coupling processes [42][43][44]. However, these methods have only delivered a narrow range of derivatives. Prior to application in Pd-catalyzed processes

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

• Lucie Brulikova and
• Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

• compound should serve as a molecular probe that facilitates selective detection of excess electron transfer or hole migration in DNA using gel electrophoresis. The synthesis of the desired phosphoramidite 150 (Scheme 25) started with the Pd-catalyzed cross-coupling of 5-iodo-2'-deoxyuridine (14) and a

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• . Coupling reactions Pd-catalyzed cross-coupling reactions were carried out in direct aqueous miniemulsions with 1,2,4-tribromobenzene as crosslinker [132]. Aqueous latexes of crosslinked poly(p-phenylene ethynylene) were obtained and their opto-electronic properties were found to be similar to the linear

Recent progress on the total synthesis of acetogenins from Annonaceae

• Nianguang Li,
• Zhihao Shi,
• Yuping Tang,
• Jianwei Chen and
• Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48