Search results

Search for "alkyne" in Full Text gives 595 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study

  • Angel Ho,
  • Austin Pounder,
  • Krish Valluru,
  • Leanne D. Chen and
  • William Tam

Beilstein J. Org. Chem. 2022, 18, 251–261, doi:10.3762/bjoc.18.30

Graphical Abstract
  • explanation towards the sole production of the experimentally observed anti-acylated product 15. Although Weller and co-workers have elegantly demonstrated hydride migration, rather than the alternative carbometalation, occurs during rhodium-catalyzed intermolecular alkyne hydroacylation [78], no such
PDF
Album
Supp Info
Full Research Paper
Published 02 Mar 2022

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

  • Peterson de Andrade,
  • Sanaz Ahmadipour and
  • Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

Graphical Abstract
  • sialic acid derivatives in good yields and high purity via copper-catalysed azide–alkyne cycloaddition (CuAAC, click chemistry) and evaluated their activity towards TcTS and neuraminidase. Surprisingly, the compounds showed practically no TcTS inhibition, whereas ca. 70% inhibition was observed for
  • ) has also been introduced at C-2 of α-triazole-linked sialic acid derivatives modified at C-9 as ligands for the transmembrane glycoprotein CD22 [21]. In this sense, we have synthesised a small series of 1,2,3-triazole-linked sialic acid derivatives via copper-catalysed azide–alkyne cycloaddition
  • steps from N-acetylneuraminic acid [26] – and terminal alkyne (72 µmol) in DMF/H2O 4:1 (1 mL) in a glass vial. The mixture was stirred for 24 h at 60 °C [33] and solvents were evaporated under vacuum with addition of toluene (3 × 5 mL). EtOAc (10 mL) was added to the crude and washed with H2O (3 × 5 mL
PDF
Album
Supp Info
Full Research Paper
Published 17 Feb 2022

Earth-abundant 3d transition metals on the rise in catalysis

  • Nikolaos Kaplaneris and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2022, 18, 86–88, doi:10.3762/bjoc.18.8

Graphical Abstract
  • syntheses, crop protection or medicinal chemistry. Particularly, cross-coupling reactions [1], as well as alkene and alkyne metathesis [2][3], have considerably changed the art of molecular synthesis, with a major impact on neighboring disciplines, such as molecular biology or materials sciences. Despite of
PDF
Editorial
Published 07 Jan 2022

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

Graphical Abstract
PDF
Album
Review
Published 07 Dec 2021

Electrocatalytic C(sp3)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis

  • Bin Guo and
  • Hai-Chao Xu

Beilstein J. Org. Chem. 2021, 17, 2650–2656, doi:10.3762/bjoc.17.178

Graphical Abstract
  • electrosynthesis was conducted in a microreactor equipped with two Pt electrodes as the anode and cathode and operated with a constant current (Table 1). Under the optimized conditions, a solution of tetrahydroisoquinoline 1a (1 equiv), alkyne 2 (1.5 equiv), Cu(OTf)2 (10 mol %), TEMPO (20 mol %), n-Bu4NPF6 (0.2
  • electrosynthesis was investigated by varying the substituents of the tetrahydroisoquinoline and the alkyne (Scheme 2). The N-phenyl ring of the tetrahydroisoquinoline could be substituted with groups such as OMe (4, 5), Me (6), Et (7), t-Bu (8), F (9), and Cl (10). An N-2-naphthalenyl-substituted
  • tetrahydroisoquinoline bearing two OMe groups at 6,7-positions (11) also reacted successfully. The alkyne coupling partner also tolerated variation. The reactions were found to be compatible with arylalkynes such as phenylacetylenes bearing at the para position a H (12), Me (13), t-Bu (14, 16), or Br (15), 2
PDF
Album
Supp Info
Letter
Published 28 Oct 2021

Visible-light-mediated copper photocatalysis for organic syntheses

  • Yajing Zhang,
  • Qian Wang,
  • Zongsheng Yan,
  • Donglai Ma and
  • Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

Graphical Abstract
  • complexes to photocatalysis are reported. Copper-photocatalyzed reactions, including alkene and alkyne functionalization, organic halide functionalization, and alkyl C–H functionalization that have been reported over the past 5 years, are included. Keywords: copper-photocatalyzed reactions; green chemistry
  • ruthenium-based catalysts and copper-based catalysts are discussed, and the strong reduction ability of copper complexes is explained. Subsequently, mechanisms of the photoredox catalysis by CuI and CuII are summarized, and the copper-catalyzed reactions, including alkene functionalization, alkyne
  • bonds and can be applied to radical chemistry. This review discusses copper-catalyzed reactions including alkene and alkyne, organic halide, and alkyl C–H functionalization. 3. Visible-light-mediated copper-catalyzed alkene and alkyne functionalization 3.1 Olefinic C–H functionalization and allylic
PDF
Album
Review
Published 12 Oct 2021

Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines

  • Zhen-Sheng Jia,
  • Qiang Yue,
  • Ya Li,
  • Xue-Tao Xu,
  • Kun Zhang and
  • Bing-Feng Shi

Beilstein J. Org. Chem. 2021, 17, 2488–2495, doi:10.3762/bjoc.17.165

Graphical Abstract
  • derivatives were also developed by the groups of You [30], Ackermann [31] and Shi [32][33] with 1,4,2-dioxazol-5-ones as versatile amidating reagents. In 2019, the alkynylated ferrocenes were isolated in the formation of alkyne-Cu(I) π-complexes by the Tan group via Cu-mediated C–H alkynylations [34]. Later
PDF
Album
Supp Info
Letter
Published 28 Sep 2021

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

  • Azra Kocaarslan,
  • Zafer Eroglu,
  • Önder Metin and
  • Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

Graphical Abstract
  • , Turkey King Abdulaziz University, Faculty of Science, Chemistry Department, 21589 Jeddah, Saudi Arabia 10.3762/bjoc.17.164 Abstract The development of long-wavelength photoinduced copper-catalyzed azide–alkyne click (CuAAC) reaction routes is attractive for organic and polymer chemistry. In this study
  • its conduction (CB) and valence band (VB), respectively. The excited electrons thus formed were then transferred to the CuII ions to produce active CuI catalysts. The ability of BPNs to initiate the CuAAC reaction was investigated by studying the reaction between various low molar mass alkyne and
  • [40]. BPNs were tested as NIR photoinitiator for the CuAAC reactions of low molar mass compounds and polymers possessing antagonist azide and alkyne functionalities (Figure 1). The optical absorption spectra of BPNs, copper(I) chloride (CuICl, 0.05 mmol) and copper(II) chloride (CuIICl2, 0.05 mmol
PDF
Album
Supp Info
Full Research Paper
Published 23 Sep 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

Graphical Abstract
  • -annulation reaction may undergo a free-radical addition pathway. Firstly, NFSI oxidizes Cu(I) to form bissulfonylamidyl radical 10. Secondly, intermolecular nitrogen free-radical addition to the alkyne provides the vinyl radical 11. Then, there may be two possible pathways. Path a: vinyl radical 11 is
  • be carried out at 90 °C in 8 h to provide the 5-sulfenyl-substituted nicotinates 19 efficiently. Based on previous literature and control experiments, the possible mechanism is outlined in Scheme 8. First, the Cu-complex-polarized X−X bond can promote the electrophilic addition onto the alkyne to
  • esterified pyridines 29 in moderate to high yield. It is worth noting that 1,3-enynes 28 bearing internal alkyne moieties were not tolerated as substrates. In 2016, Aïssa and co-workers reported a nickel-catalyzed [4 + 2]-cycloaddition of 3-azetidinones 30 with 1,3-enynes 31 for the synthesis of 3‑hydroxy
PDF
Album
Review
Published 22 Sep 2021

Strategies for the synthesis of brevipolides

  • Yudhi D. Kurniawan and
  • A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

Graphical Abstract
  • esterification step. In the retrosynthesis, compound 107 is conceived as the branching intermediate to access both brevipolides M and N (Scheme 13). The 5,6-dihydro-α-pyrone moiety can be derived from alkyne 108 via the sequential deprotection, Lindlar reduction, and oxidation. The propargylic alcohol moiety is
PDF
Album
Review
Published 14 Sep 2021

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

  • Satya Kumar Avula,
  • Syed Raza Shah,
  • Khdija Al-Hosni,
  • Muhammad U. Anwar,
  • Rene Csuk,
  • Biswanath Das and
  • Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

Graphical Abstract
  • . The structure of metronidazide 3 was unambiguously confirmed by single crystal X-ray analysis (Figure 3). The next step was carried out by using “click” chemistry involving the 1,3-dipolar cycloaddition reaction between metronidazide 3 and alkyne derivative 4a in the presence of CuI and Hünig’s base
  • , analogues 5b–i were obtained in 86–94% yield using the different alkyne derivatives 4b–i. The synthesis of the new 1H-1,2,3-triazole derivatives of metronidazole is summarized in Scheme 1 and Table 1. Their chemical structures (5a–i) were confirmed by spectroscopic techniques (1H NMR, 13C NMR) and HRMS. The
  • compounds 5a–i and 7a–e. Reagents and conditions: (a) TsCl, Et3N, dry DCM, DMAP, 0 °C to room temperature, 5 h, 96%; (b) NaN3, DMF, 70 °C, 3 h, 88%; (c) alkyne derivative (4a–i), CuI, Et3N, CH3CN, room temperature, 3 h, (5a–i) 85–94%. Reagents and conditions: (a) acid chlorides 6a–e, pyridine, dry DCM, DMAP
PDF
Album
Supp Info
Full Research Paper
Published 09 Sep 2021

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

Graphical Abstract
  • the alkyne may be influenced by diastereomers; in the case of cis-isomer 82 exocyclic enol ether 83 was formed while for trans-isomer 84 the reaction takes place with a much slower rate yielding endocyclic enol ether 85 as the only product (Scheme 27) [79]. trans-Acetylenic alcohol 86 on treatment
  • arylacetylenes 93, 95, and 97 yielded benzofurans 94, benzothiophenes 96, and indoles 98, respectively. When the carbonyl group was introduced between an aryl and a methoxy group (99) then six-membered isocoumarin ring 100 was formed, and when a carbonyl group was introduced in between an aryl and an alkyne
  • HgCl2-mediated cyclization reaction of tethered alkynedithioacetals 110 to provide six- and five-membered carbocyclic and heterocyclic derivatives 111 and 112, respectively. They had observed that the formation of five-membered rings (112a–c) was preferred when substitutents were present at the alkyne
PDF
Album
Review
Published 09 Sep 2021

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

  • Songeziwe Ntsimango,
  • Kennedy J. Ngwira,
  • Moira L. Bode and
  • Charles B. de Koning

Beilstein J. Org. Chem. 2021, 17, 2340–2347, doi:10.3762/bjoc.17.152

Graphical Abstract
  • ], rhodium-mediated alkyne [2 + 2 + 2] cycloaddition reactions [3], and the palladium-catalysed aerobic domino Suzuki coupling/Michael addition reaction [4]. The most attractive and common strategies to phenanthridines rely on intramolecular cyclizations of various ortho-functionalized biaryl precursors
PDF
Album
Supp Info
Full Research Paper
Published 08 Sep 2021

Photoredox catalysis in nickel-catalyzed C–H functionalization

  • Lusina Mantry,
  • Rajaram Maayuri,
  • Vikash Kumar and
  • Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

Graphical Abstract
  • /arylation of cyclic oxalates 33 with terminal alkyne 34 and aryl bromides 3 (Scheme 20) [73]. As to the scope, aryl bromides 3 containing various electron-withdrawing substituents displayed better efficiency over the electron-rich aryl bromides. The authors proposed a plausible catalytic cycle to account
  • ) photocatalyst 10-III. The active iridium(III) photocatalyst 10-I is regenerated by a SET process between 10-III and the nickel(I) species 10-X. The addition of the tertiary radical 10-IV to the terminal alkyne 34 followed by an intramolecular 1,5-HAT results in a nucleophilic secondary alkyl radical species 10
PDF
Album
Review
Published 31 Aug 2021

Recent advances in the syntheses of anthracene derivatives

  • Giovanni S. Baviera and
  • Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

Graphical Abstract
  • monofunctionalized naphthyl substrates. These authors demonstrated that the rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids 7 with alkyne 8 occurred in the presence of a copper–air oxidant, to give the corresponding 1,2,3,4-tetrasubtituted anthracene derivatives 9a and 9b (Scheme 1) [34
  • aromatic ring were well tolerated during the cyclization, affording the corresponding anthracenes 14a–d. The authors expanded the scope of the reaction to internal alkyne substrates and obtained the corresponding substituted anthracenes. The most representative examples included compounds 14e–h [36]. In
  • methodology was notable for being an alternative method to synthesize 2,3,6,7-halogenated anthracene derivatives, which are difficult to obtain. In 2010, Okamoto et al. published a three-step procedure to synthesize substituted anthracenes, pentaphenes, and trinaphthylenes via a [2 + 2 + 2] alkyne
PDF
Album
Review
Published 10 Aug 2021

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

  • Mathias B. Danielsen and
  • Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

Graphical Abstract
  • containing a stretch of four DNA nucleotides in the middle, flanked by the modifications in a ´mixmer´ design, which is important for designing gapmer ASOs [31]. Another well-established method for C-5 pyrimidine modification involves the Sonogashira cross-coupling reaction between an alkyne group and a 5
  • -iodo-modified nucleobase/nucleoside followed, if desired, by reduction [44] to give a more flexible group, or the alkyne group can be retained, depending on the modification needed [45][46][47]. This method has been extensively used to study various modifications, and some of them can be seen in Table
PDF
Album
Review
Published 29 Jul 2021

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

  • Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

Graphical Abstract
  • conjugative transformations, such as azide–alkyne [3 + 2]-cycloaddition [30][31][32][33][34][35][36][37]. Based on their previous late-stage fluorination studies [22][25], Groves et al. further showcased a manganese(III)–salen-catalyzed azidation process using an aqueous azide solution as a convenient azide
  • ). Based on additional mechanistic investigations, it was proposed that substrate 23 forms five-membered manganacycle complex 23A under basic conditions, which undergoes alkyne insertion to provide seven-membered manganacycle complex 23B (Figure 7). Subsequently, intermediate 23B undergoes β-bromo
PDF
Album
Review
Published 26 Jul 2021

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

  • Susanne M. Fischer,
  • Simon Renner,
  • A. Daniel Boese and
  • Christian Slugovc

Beilstein J. Org. Chem. 2021, 17, 1689–1697, doi:10.3762/bjoc.17.117

Graphical Abstract
  • , in this case, the activity of the catalyst is not rate determining. This observation is rationalized by the occurrence of a non-productive acid–base equilibrium involving the de- and re-protonation of the considerably acidic alkyne proton in d (pKa = 15.61 [20]) [21]. The reaction conditions
PDF
Album
Supp Info
Full Research Paper
Published 21 Jul 2021

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

Graphical Abstract
  • -catalyzed azide–alkyne cycloaddition (CuAAC) for the synthesis of 1,4-disubstituted 1,2,3-triazole derivatives was initially discovered by the groups of Meldal and Sharpless. Then, Ru-catalyzed azide–alkyne cycloaddition (RuAAC), affording selectively 1,5-disubstituted 1,2,3-triazoles, was introduced [38
  • decrease in the yield [47]. Some research groups have utilized strain-promoted azide–alkyne cycloaddition reactions (SPAAC) on side chains to afford polymer-based prodrugs. Generally, a range of key strained cyclooctyne derivatives 52 could be reacted with aliphatic azides 51 via this strategy to give
  • bond of an alkyne into the Cu–triazole bond gives 64, which then undergoes syn-β-oxygen elimination to provide the target product. On the other hand, an oxidative addition and reductive elimination sequence can also generate the target product (Scheme 20) [50]. An immobilized copper complex has been
PDF
Album
Review
Published 13 Jul 2021

Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

  • Feng Xiong,
  • Bo Li,
  • Chenrui Yang,
  • Liang Zou,
  • Wenbo Ma,
  • Linghui Gu,
  • Ruhuai Mei and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

Graphical Abstract
  • alkyne annulation was very recently achieved by Ackermann et al., which gave rapid access to synthetically meaningful isoindolones (Figure 1c) [34]. In spite of these indisputable advances, the successful removal of the directing groups to deliver the free-NH 3-methyleneisoindolin-1-one has thus far
  • alkyne 2a and a stoichiometric amount of Cu(OAc)2 in DMSO (Table 1, entries 1–3). Reaction optimization revealed that the most appropriate temperature was 90 °C (Table 1, entries 3–6). An evaluation of bases showed that Na2CO3 was optimal (Table 1, entries 7–11). The best result was obtained when Cu(OAc
  • complex mixture was observed when an aliphatic terminal alkyne was used, and no annulation product was detected for internal alkynes. Our copper-promoted C−H annulation protocol was not restricted to terminal alkynes. Under identical reaction conditions, commercially available alkynylcarboxylic acid 4
PDF
Album
Supp Info
Full Research Paper
Published 08 Jul 2021

Double-headed nucleosides: Synthesis and applications

  • Vineet Verma,
  • Jyotirmoy Maity,
  • Vipin K. Maikhuri,
  • Ritika Sharma,
  • Himal K. Ganguly and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Graphical Abstract
  • -ethynylpyrene (40) under copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction conditions to yield the double-headed nucleoside 41 (Scheme 10) [23]. The double-headed nucleoside 41 was phosphitylated and then incorporated into oligonucleotides and was found to form highly stable DNA duplexes and three
  • nucleosides were further reacted with propargylated nucleobases through a copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction followed by treatment with methanolic ammonia to give the C-3′-substituted double-headed ribofuranonucleosides 46a–c and 50a–e (Scheme 11) [36]. The double-headed nucleosides
  • ]. Hrdlicka and co-workers [24] also synthesized 5-C-triazolyl-functionalized double-headed nucleosides 154a,b starting from 5-C-ethynyl-functionalized LNA uridine 152. The LNA uridine 152 was reacted with 1-azidopyrene (153a) and 1-azidomethylpyrene (153b) separately under copper-catalyzed alkyne azide
PDF
Album
Review
Published 08 Jun 2021

Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

  • Tsutomu Kimura,
  • Koto Sekiguchi,
  • Akane Ando and
  • Aki Imafuji

Beilstein J. Org. Chem. 2021, 17, 1352–1359, doi:10.3762/bjoc.17.94

Graphical Abstract
  • magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations. Keywords: alkyne; 1-chlorovinyl p-tolyl sulfoxide; DFT calculation; Fritsch–Buttenberg–Wiechell rearrangement; magnesium alkylidene carbenoid; Introduction Alkynes are important compounds in organic
  • )magnesium chlorides, CH2=CXMgCl (X = F, Cl, and Br) << (1-chlorovinyl)lithium, CH2=CClLi. If the 1-heteroatom-substituted vinylmetal displays vinylidene characteristics, the FBW rearrangement occurs to give the alkyne. If not, the vinylmetal is simply protonated to give a heteroatom-substituted alkene. A
  • p-tolyl sulfoxide and alkyne 4a were obtained in 97% yield and 99% yield, respectively. This result shows that both the sulfoxide/magnesium exchange reaction and the FBW rearrangement occurred with high efficiency. A similar reaction of sulfoxide 2a with sec-butyllithium also gave alkyne 4a in 97
PDF
Album
Supp Info
Full Research Paper
Published 28 May 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Graphical Abstract
PDF
Album
Review
Published 18 May 2021

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

  • Asha Budakoti,
  • Pradip Kumar Mondal,
  • Prachi Verma and
  • Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

Graphical Abstract
  • (Scheme 55). The methodology of alkynylsilane Prins cyclization was explored for the synthesis of 2,6-dihydropyran 238 by reacting secondary homopropargyl alcohol 236, having a trimethylsilyl group at the triple bond, with an aldehyde (Scheme 56) [98][99][100][101]. The reaction follows alkyne Prins
  • -trimethylsilylalkenyl cation 242 formed by the Grob-type fragmentation (Scheme 57), which was trapped by the subsequent attack of the halide anion, leading to the formation of Prins product 244. On the basis of theoretical calculations, the authors could conclude factors controlling the alkyne Prins cyclization over
PDF
Album
Review
Published 29 Apr 2021

Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

  • Dat Phuc Tran,
  • Yuki Sato,
  • Yuki Yamamoto,
  • Shin-ichi Kawaguchi,
  • Shintaro Kodama,
  • Akihiro Nomoto and
  • Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

Graphical Abstract
  • variety of terminal alkynes including both alkyl- and arylalkynes. Keywords: (E)-1,2-bis(diphenylphosphino)ethylene derivative; radical addition; stereoselective phosphinylphosphination; terminal alkyne; tetraphenyldiphosphine monoxide; Introduction Organophosphorus compounds are an essential class of
  • absorption is located at a shorter wavelength (λmax = 318 nm) and the absorption intensity is lower than those of Ph2PPPh2 and Ph2P(S)PPh2 [46]. Indeed, the photoinduced addition of Ph2P(O)PPh2 to alkynes required prolonged reaction times (>40 h), and the scope of this alkyne addition was unexamined. Thus
  • inhibited the desired phosphinylphosphination (see, alkyne 2f), probably because of the decomposition of Ph2P(O)PPh2. Furthermore, an electron-deficient alkyne such as methyl propiolate (2h) failed to provide the desired adduct (3h) [61]. 3-Phenyl-1-propyne (2i) and cyclohexylacetylene (2j) gave 3i and 3j
PDF
Album
Supp Info
Full Research Paper
Published 20 Apr 2021
Other Beilstein-Institut Open Science Activities