New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

• Adam Mondrzyk,
• Beate Mondrzik,
• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

• (N3-β-CD) was carried out. The formation of inter- and intramolecular inclusion complexes was investigated by DLS measurement. Keywords: copolymer; ß-cyclodextrin; enzymatic polymerization; 4-ferrocenylphenol; polyphenol; 4-tert-butylphenol; horseradish peroxidase; HRP oxidative coupling; inclusion

Rh(III)-catalyzed directed C–H bond amidation of ferrocenes with isocyanates

• Satoshi Takebayashi,
• Tsubasa Shizuno,
• Takashi Otani and
• Takanori Shibata

Beilstein J. Org. Chem. 2012, 8, 1844–1848, doi:10.3762/bjoc.8.212

• enantioselective if chiral bisoxazoline ligands were used. However, the substrate scope of this reaction is narrow because of intramolecular reaction. More recently, chiral oxazoline-directed diastereoselective arylation of ferrocenes was reported based on a Pd(II)-catalyzed oxidative coupling reaction [8]. Most

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• order to achieve reoxidation of the Pd(0) species to Pd(II). Intramolecular reactions involving arenes Intramolecular arylations by oxidative coupling were investigated by DeBoef and co-workers as a tool for synthesizing heteropolycyclic compounds [80]. The aerobic Pd(II)-catalyzed reaction of the N

• (Scheme 32) [79]. Indeed, the reaction carried out with 10 mol % of PdCl2(MeCN)2 as catalyst and a stoichiometric amount of 1,4-benzoquinone in DMF/THF as solvent underwent an oxidative cascade process involving the sequential intramolecular formation of C–N and C–C bonds, with an oxidative coupling

Synthesis of conformationally restricted glutamate and glutamine derivatives from carbonylation of orthopalladated phenylglycine derivatives

• Esteban P. Urriolabeitia,
• Eduardo Laga and
• Carlos Cativiela

Beilstein J. Org. Chem. 2012, 8, 1569–1575, doi:10.3762/bjoc.8.179

• processes and avoiding the obtainment of unwanted isomers. Probably the aspect of this method of synthesis with the greatest impact is the oxidative coupling of two C–H bonds to give a new C–C bond, because it avoids the use of prefunctionalized substrates, minimizes the amount of waste generated during the

Arylglycine-derivative synthesis via oxidative sp³ C–H functionalization of α-amino esters

• Zhanwei Xu,
• Xiaoqiang Yu,
• Xiujuan Feng and
• Ming Bao

Beilstein J. Org. Chem. 2012, 8, 1564–1568, doi:10.3762/bjoc.8.178

• Zhanwei Xu Xiaoqiang Yu Xiujuan Feng Ming Bao State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, China 10.3762/bjoc.8.178 Abstract An efficient method for the synthesis of arylglycine derivatives is described. The oxidative coupling reactions of naphthols and

• reported the copper-catalyzed oxidative coupling reaction of alkynes with tertiary amine N-oxides [15]. This new strategy for the direct functionalization of sp3 C–H bonds adjacent to a nitrogen atom, via tertiary amine N-oxide intermediates, was successfully applied to the coupling reaction of ethyl 2

• -1-yl)acetate (2b), and ethyl 2-(benzyl(methyl)amino)acetate (2c) proceeded smoothly to give the corresponding products 3a–3c in good yields (Table 2, entries 1–3, 64–79%). These results indicated that both α-cyclic and acyclic amino esters could be employed in this type oxidative coupling reaction

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

• study the role of the dimethylaminophenyl group on the oligothiophene properties. The synthesis of 2a and 2b was completed by following our published procedure [14], with oxidative coupling of 3a or 3b with the aid of FeCl3 affording sexithiophenes 2a and 2b in moderate yields (40% and 50%, respectively

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira–Glaser cyclization sequence

• Dominik Urselmann,
• Dragutin Antovic and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1499–1503, doi:10.3762/bjoc.7.174

• yields, resulting in an increased formation of byproducts already during the desilylation and the oxidative coupling step (as monitored by TLC). A lower reaction temperature resulted in a prolonged reaction time under microwave conditions to achieve complete conversion (Table 1, entry 5), whereas

Ugi post-condensation copper-triggered oxidative cascade towards pyrazoles

• Aurélie Dos Santos,
• Laurent El Kaim,
• Laurence Grimaud and
• Caroline Ronsseray

Beilstein J. Org. Chem. 2011, 7, 1310–1314, doi:10.3762/bjoc.7.153

• pyrazolidinone under oxidative conditions from simple hydrazone derivatives (Scheme 1) [13]. The cascade features a [3 + 2] cycloaddition coupled with an aerobic oxidation of the resulting pyrazolidine. A further oxidative coupling may be observed according to the substitution pattern of the starting acyl

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

• chloranil amidocuprate 87 undergoes an oxidative coupling providing the adenine derivative 88 in 71% yield. A treatment with D-valinol (89) affords the desired CDK inhibitor, purvalanol A (84) in 65% yield (Scheme 15) [44]. 2.2 The preparation of polyfunctional heterocyclic magnesium reagents by the

Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes

• Marco Blangetti,
• Patricia Fleming and
• Donal F. O'Shea

Beilstein J. Org. Chem. 2011, 7, 1249–1254, doi:10.3762/bjoc.7.145

• oxidative coupling with 1,2-dibromoethane. The synthetic ease of this approach compares favourably with previously reported methods and allows for ready access to potentially useful planar chiral derivatives. Keywords: benzylic metalation; LiNK chemistry; [2.2]metacyclophane; oxidative coupling; planar

• ]. We envisaged that our LiNK metalation conditions with in situ oxidative coupling could offer a facile general approach to [2.2]metacyclophanes, which would be of general synthetic interest (Scheme 2). Oxidative homo-coupling of benzyl anions has previously been noted, but it has remained relatively

• unexplored as a synthetic procedure [22][23][24]. We speculated that if oxidative coupling of the benzyl metalated xylenes 5 could be achieved to form the open dimer 6, then a second metalation and oxidative ring closure would yield the [2.2]metacyclophanes 8. A stepwise approach, as shown in Scheme 2, could

Novel carbazole–pyridine copolymers by an economical method: synthesis, spectroscopic and thermochemical studies

• Aamer Saeed,
• Madiha Irfan and
• Shahid Ameen Samra

Beilstein J. Org. Chem. 2011, 7, 638–647, doi:10.3762/bjoc.7.75

• of the pyridine ring [20]. Zheng et al. have prepared a new class of copolymers that incorporate pyridine and N-alkyl carbazole alternatively into the main chain by oxidative-coupling copolymerization. These polymers are thermostable, highly soluble, and processable, and the fluorescence spectra of

Gold catalysis for organic synthesis

• F. Dean Toste

Beilstein J. Org. Chem. 2011, 7, 553–554, doi:10.3762/bjoc.7.63

• , cycloaddition and cycloisomerization reactions, to applications in enantioselective catalysis, oxidative coupling and the total synthesis of natural products, and transformations of alkynes, allenes, alkenes and even C–H bonds. A true treasure chest of reactivity! I am grateful to all of the authors that have

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• -oxidative coupling of 3 and 27 is therefore only accessible through the pendant group making a dimer the only possible product. Compounds 25 and 28 have two oxidisable pendant thiophene groups, so polymerisation could theoretically proceed through the coupling of these units. However, repeated cycling over

Pd/C- Mediated synthesis of indoles in water

• Mohosin Layek,
• Udaya Lakshmi,
• Dipak Kalita,
• Deepak K. Barange,
• Aminul Islam,
• K. Mukkanti and
• Manojit Pal

Beilstein J. Org. Chem. 2009, 5, No. 46, doi:10.3762/bjoc.5.46

• present study we have used three equivalents of terminal alkynes to obtain the optimum yields of products. It is possible that the excess equivalents of terminal alkynes might undergo dimerization via oxidative coupling though no significant amount of 1,3-butadiyne derivative was isolated as a side