Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• authors do not justify the selection of the particular substitution pattern with the C6 methyl and the C2 heteroatom methyl, e.g., ease of access to this type of DHPM core. Therefore, it would be interesting to see whether this method is compatible with other DHPM systems. In the same publication, the

• regioselective and follows the same substitution pattern as the electrophilic substitution of electron-rich heterocycles. Although highly elaborated structures are not presented, the mild reaction conditions and general functional group compatibility that the reaction exhibits make it well suited for LSF

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

• Siva Sankar Murthy Bandaru,
• Darinka Dzubiel,
• Heiko Ihmels,
• Mohebodin Karbasiyoun,
• Mohamed M. A. Mahmoud and
• Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

• [14][15][16][17][18] and whose interaction with the nucleic acid may be used for fluorimetric detection of the latter [19][20]. To further exploit the DNA-binding properties of this specific class of cationic hetarenes, synthetic routes to novel derivatives with the desired substitution pattern and

The phenyl vinyl ether–methanol complex: a model system for quantum chemistry benchmarking

• Dominic Bernhard,
• Fabian Dietrich,
• Mariyam Fatima,
• Cristóbal Pérez,
• Hannes C. Gottschalk,
• Axel Wuttke,
• Ricardo A. Mata,
• Martin A. Suhm,
• Melanie Schnell and
• Markus Gerhards

Beilstein J. Org. Chem. 2018, 14, 1642–1654, doi:10.3762/bjoc.14.140

• OH∙∙∙O structure was identified. In a systematic study by the Suhm group on complexes of anisole derivatives with methanol, a balance between OH∙∙∙O and OH∙∙∙π structures being very sensitive to the substitution pattern at the anisole moiety was identified [17][18]. In previous multi-spectroscopic

Direct electrochemical generation of organic carbonates by dehydrogenative coupling

• Tile Gieshoff,
• Vinh Trieu,
• Jan Heijl and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2018, 14, 1578–1582, doi:10.3762/bjoc.14.135

• studies on a potential scope of aromatic compounds, the symmetric 1,3,5-threefold substitution pattern showed best selectivity according to GC–MS measurements. Since the nucleophilic attack is controlled by sterics, non-symmetric substitution patterns gave weak signals and product mixtures. Generally, the

• nucleophilicity of carbonates is limited and therefore, the choice of suitable arenes is crucial. Heterofunctionalizations like fluoro, chloro, and methoxy groups are generally accepted, but it depends on the substitution pattern. The sensitive interplay of inefficient oxidation at highly positive oxidation

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• group of Chi [16] who has recently described a series of neutral platinum(II) complexes bearing isoquinolylpyrazolates, complexes 4–7 in Figure 3 [26]. Control on the intermolecular interactions was exerted through the substitution pattern, yielding solids that exhibited mechano- and solvatochromic

Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups

• Cyrus Mowdawalla,
• Faiz Ahmed,
• Tian Li,
• Kiet Pham,
• Loma Dave,
• Grace Kim and
• I. F. Dempsey Hyatt

Beilstein J. Org. Chem. 2018, 14, 1039–1045, doi:10.3762/bjoc.14.91

• group. The latter of which would be consistent with the mechanism currently theorized for making alkenyl and alkynyl hypervalent iodine species [18][19][20][21][22]. While investigating the substrate scope it was found that the substitution pattern is dependent upon the substituents on the I(III

• the use of BF3·Et2O seemed to be superior to Tf2O in the case of some I(III) reactants. In all the reactions tested, there were no products formed with the ortho-substitution pattern in contrast to the RICR, however, it is clear that electron-donating groups influence the ring substitution. When

• ). These key features in the substitution pattern of the substrate scope led to experiments where tests were performed to better understand, if the HIGES reaction is a concerted mechanism, like RICR, or a stepwise process. In the article and further in a footnote of Khatri and Zhu’s publication [11

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

• Robby Vroemans,
• Fante Bamba,
• Jonas Winters,
• Joice Thomas,
• Jeroen Jacobs,
• Luc Van Meervelt,
• Jubi John and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

• , we investigated the effect of the substitution pattern on the propargylamine 2. For this, we chose easily available propargylamines 2b and 2c which gave moderate to good yields (60 and 40%, respectively) of diketopiperazine-fused triazolobenzodiazepine 7e and 7f. Furthermore, halogen substituents

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

• substitution pattern of the carbazole unit on the photophysical properties. While maintaining the same number of carbazole units on the emitter and by varying the substitution pattern of the carbazole core, only a weak influence on the EL characteristics was evidenced [55]. In fact, performances only varied by

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• sulfenylated dienes by dehydration. A series of aryl thiols with different steric and electronic properties give high yields of the thiol–yne products. Noteworthy is the high E-selectivity of the resulting alkene. Dependent on the substitution pattern of the aryl thiol a ratio up to 60:1 was observed due to

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF₃SO₂Cl

• Hélène Chachignon,
• Hélène Guyon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

• also suitable to carry out this reaction [12]. The same tendencies in term of reactivity of the substrates depending on their substitution pattern was observed, and similar yields were achieved (Scheme 10). Similarly, Ir(ppy)2(dtbbpy)PF6 was also described as an appropriate catalyst for this cascade

• selectively place from a direction anti to the CF3 group, probably because of electrostatic repulsion. The reaction proceeded smoothly with prop-1-yn-1-ylbenzene derivatives, indifferently to the substitution pattern of the aryl moiety. As for the R group, alkyl, ester or amide moieties were well-tolerated

Synthesis of 1,3-cis-disubstituted sterically encumbered imidazolidinone organocatalysts

• Jan Wallbaum and
• Daniel B. Werz

Beilstein J. Org. Chem. 2017, 13, 2577–2583, doi:10.3762/bjoc.13.254

• subtle differences in the substitution pattern a modular approach for their preparation is highly desirable. A simple retrosynthetic cut of the five-membered ring delivers an amino acid methyl amide and a carbaldehyde as starting materials. Chirality is commonly introduced by the use of derivatives of

Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity

• Tathagata Mukherjee,
• Soumik Biswas,
• Andreas Ehnbom,
• Subrata K. Ghosh,
• Ibrahim El-Zoghbi,
• Nattamai Bhuvanesh,
• Hassan S. Bazzi and
• John A. Gladysz

Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246

• substitution pattern was evident from the 1H NMR spectrum. When Cl2 gas was sparged through a CF3C6H5 solution of 1,3,5-(Rf6)2C6H3I at −30 °C to −35 °C, the sample turned bright yellow. Two aliquots were removed. The 1H NMR spectrum of one (Figure 1b) showed two downfield shifted signals (cf. Figure 1a), which

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• can be detected and monitored by absorption and emission spectroscopy. Furthermore, the investigation of a substance library of various 2,3- and 1,8-naphthalene imides has shown that the electronic nature of the ground and the excited state is decisively influenced by variation of the substitution

• pattern of the naphthalene scaffold. Even the smallest polarity change in the solvent system effects their absorption and emission behavior [34][40]. Very recent investigations on naphthaleneimide derivatives revealed enormous phosphorescence lifetimes that are particularly interesting for imaging

Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

• Grzegorz Mlostoń and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221

• - and Z-1b, and depending on the substitution pattern of the aziridine ring, the formation of the pyrrolidine derivative 34 occurred either with complete stereoselectivity or mixtures of isomeric products were obtained. The [3 + 2]-cycloaddition of the azomethine ylide E,Z-32a, formed via conrotatory

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Base-promoted isomerization of CF₃-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions

• Yoko Hamada,
• Tomoko Kawasaki-Takasuka and
• Takashi Yamazaki

Beilstein J. Org. Chem. 2017, 13, 1507–1512, doi:10.3762/bjoc.13.149

• intermolecular reprotonation by the solvent. The present interesting proton shift reaction was also computationally simulated [7] by employing (R,E)-6h with the substitution pattern of R1 = Ph and R2 = Me as the model substrate. For simplicity, 1,4-diazabicyclo[2.2.2]octane (DABCO) was employed as the

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

• Kohei Yamada,
• Naoto Kamimura and
• Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

• substitution pattern at the 4-position of the oxazole. The one-pot oxazole synthesis with phenylalanine (2b), valine (2c), leucine (2d), methionine (2e), and phenylglycine (2f) proceeded to give the corresponding intermediates in good yields (Table 1, entries 6–10). Despite the existence of highly polar

Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

• Manuel Anselmo,
• Lisa Moni,
• Hossny Ismail,
• Davide Comoretto,
• Renata Riva and
• Andrea Basso

Beilstein J. Org. Chem. 2017, 13, 1456–1462, doi:10.3762/bjoc.13.143

• isochromanone 4a in 72% yield (Scheme 2 and Table 1). Analogous results were obtained when the substitution pattern on both the diazonium salt and the alkene was varied, results that paralleled those reported by König and Fagnoni [5]. In our hands reactions were slower (6–8 h vs 2 h), probably due to the lower

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

•  5). The tolerance of the reaction to the substitution pattern in the aromatic portion of the indolenines appears rather broad, both in terms of the electronic character of substituents and steric effects – although substituents in position 7 of the indolenine significantly affect the conformational

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• , leading to pure dialkynes with a well-defined substitution pattern. The reactivity of a pair of isomers containing a phenyl and a pentyl group attached to the triple bonds towards cycloisomerisation induced by Pt(II) catalysis was studied. The expected annulation–sulphur reduction–ring enlargement cascade

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• the substitution pattern in the carbonyl component is related with the ability of the intermediate Schiff bases to be protonated as well as with their solubility. In case of the presence of electron-withdrawing substituents in the aldehyde the corresponding Schiff bases 5 are less soluble and less

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• , the substitution pattern of the amidine moiety had little effect on the Au-catalyzed annulation reaction, whereas neutral or electron-donating groups on the aldehyde moiety gave a higher yield in comparison with the electron-withdrawing halides. Notably, bromo-substituted substrates were also

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• and small amounts of functionalized CD-LA and L-lactide monomer. All samples showed peaks for the unreacted L-lactide and separated peaks for the protons of the substituted glucopyranose units. In the 1H NMR spectra the substitution pattern of the glycoside rings of cyclodextrins can be followed by

Dimerization reactions of aryl selenophen-2-yl-substituted thiocarbonyl S-methanides as diradical processes: a computational study

• Michael L. McKee,
• Grzegorz Mlostoń,
• Katarzyna Urbaniak and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 410–416, doi:10.3762/bjoc.13.44

• convenient access comprises the treatment of a C=S substrate with diazomethane or its derivatives. Depending on the substitution pattern, 2,5-dihydro-1,3,4-thiadiazoles 2 display different thermal stability. Whereas sterically bulky aliphatic substituents increase the temperature required for the

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• as relatively low viscous, highly soluble/compatible liquids [19]. Furthermore, acrylamides are generally more reactive than the respective methacrylamides. Regarding the substitution pattern, N-monosubstituted acrylamides tend to homopolymerize more readily than their N,N-disubstituted analogues [20