Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines

• Stefan Jopp,
• Franziska Spruner von Mertz,
• Peter Ehlers,
• Alexander Villinger and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107

• first insights on how the optical properties can be fine-tuned by the substitution pattern of the arylalkyne. The key optical properties are summarized in Table 2. All molecules display relatively high quantum yields (QYs) with the highest being 0.66 for 6a and the lowest 0.54 for 12a. This is in

• on the quinoline scaffold and on the arylalkyne moiety permits the fine tuning of the optical properties. Natural and synthetic compounds containing a quinoline or quinolone core-structure. ORTEP of 6b (CCDC 2322985). ORTEP of 9f (CCDC 2322983). ORTEP of 12d (CCDC 2322984). UV–vis and emission

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• ). The products 5a–t were obtained in 95 to 25% yields, with an average yield of 56%. Furthermore, the method was shown to be highly tolerant towards different functional groups and their combinations. A higher yield tended to be observed when a donor group was located on the arylalkyne at the 6-position

• (5k, 5l, 5r). However, this effect seems to be neutralized when using an electron-rich arylboronic acid (5m). Lower yields are obtained when an acceptor group is present on the arylalkyne (5p, 5q). This leads to the suggestion that an electron-donor group activates and an electron-withdrawing group

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• reaction between an aryl/vinyl halide (Cl, Br, I, OTf) and a terminal alkyne in the presence of a Cu(I) co-catalyst under basic conditions to form a Csp2–Csp bond generating an arylalkyne is known as the Sonogashira (Sonogashira–Hagihara) coupling [1] and has become an important C–C bond-forming reaction

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

• Sumana Mandal,
• Raju D. Chaudhari and
• Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

• exemplifying benzyl derivative 160 [106]. The reported methodology was an example of the Hg(OTf)2·(TMU)3 complex promoting a moderate and efficient procedure for arylalkyne cyclization to directly afford dihydronapthalene derivatives (Scheme 47). Later, Friedel–Crafts type reaction of alkynylfuran 162 and 164

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• ), phenylacetylene (149a, 0.5 equiv) and aliphatic alkyne 149b (0.5 equiv) with tert‐butyl isocyanide (1.0 equiv) under standard reaction conditions (Scheme 42). It was found that the arylalkyne is much more reactive than the aliphatic alkyne under standard reaction conditions, giving the corresponding condensed

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

• Goki Hirata,
• Yu Yamane,
• Naoya Tsubaki,
• Reina Hara and
• Takashi Nishikata

Beilstein J. Org. Chem. 2020, 16, 502–508, doi:10.3762/bjoc.16.45

• produce 3g and 3h, respectively. An arylalkyne 1 possessing an electron-withdrawing group (ester) yielded 3i without affecting the reactivity of 2. Sulfur functional groups tend to decrease the catalytic activity of copper salts, but thienyl-substituted alkyne 1 reacted with 2a to produce 3j in 48% yield

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

• -Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

• Fabiana Pandolfi,
• Isabella Chiarotto and
• Marta Feroci

Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76

• alkyne (Et4NBF4) or the bromoalkyne (NaClO4). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction. Keywords: arylalkyne; carbon–bromine bond cleavage; cathodic reduction; Corey–Fuchs reaction; 2-(2,2-dibromovinyl)naphthalene

Microsolvation and sp²-stereoinversion of monomeric α-(2,6-di-tert-butylphenyl)vinyllithium as measured by NMR

• Rudolf Knorr,
• Monika Knittl and
• Eva C. Rossmann

Beilstein J. Org. Chem. 2014, 10, 2521–2530, doi:10.3762/bjoc.10.263

• generated arylalkyne [14] with formation of 6 and 8a. After carboxylation and aqueous work-up, the acidic product fraction contained only the arylpropiolic acid (δH = 1.56 and 7.33 ppm in CDCl3) derived from 6 but not the α-arylacrylic acid to be expected from 4. In t-BuOMe as the solvent, bromoalkene 3 was

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

• advantage of this multicomponent reaction is to suppress the isolation of the pure form of the arylalkyne derivatives, which often represents a problem due to their ability to dimerize. This one-pot four-step reaction proceeded well with a series of electron-rich and electron-poor aryl iodide derivatives

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• cyclization of the alkynylindole 251 using gold(III) chloride as the catalyst (Scheme 45). Electron-rich arenes are, in some cases, good nucleophiles [135][136]. An interesting gold-catalyzed electrophilic addition to an arylalkyne for the synthesis of substituted naphthalenes 255 has been developed [137

Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene)s and an update on the synthesis of oligoPPEs

• Dhananjaya Sahoo,
• Susanne Thiele,
• Miriam Schulte,
• Navid Ramezanian and
• Adelheid Godt

Beilstein J. Org. Chem. 2010, 6, No. 57, doi:10.3762/bjoc.6.57

• trialkylsilyl substituents simply act as steric shields for the arylalkyne. If the latter is true, then the use of 1-hydroxyethyl (HOE) or HOP instead of HOM as polar protecting groups for alkynes could prevent carbometalation. Although HOP is a sterically more demanding group, we decided in favor of HOE