1072836-40-8Relevant articles and documents
Switching of Regioselectivity in a Perfluorohexyl Iodide Mediated Synthesis of Phenylimidazo[1,2-a]pyridines
Roslan, Irwan Iskandar,Chuah, Gaik-Khuan,Jaenicke, Stephan
, p. 671 - 675 (2017)
3-Phenylimidazo[1,2-a]pyridines were synthesized through the perfluorohexyl iodide mediated coupling of 2-aminopyridines and phenylacetylenes. In situ iodination of the terminal alkyne by perfluorohexyl iodide reverses the polarity by generating a transient electrophilic iodoalkyne, and this alters the regioselectivity of the phenyl group. The reaction then proceeds by tandem electrophilic alkynylation and cyclization to form the fused-ring product. The protocol affords the 3-phenyl isomer with full regioselectivity and is complementary to reported methodologies for the synthesis of the 2-phenyl isomer starting from the same substrates.
Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling
Tatevosyan, Stepan S.,Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Lukashev, Nikolay V.,Beletskaya, Irina P.
supporting information, p. 369 - 377 (2021/10/21)
A convenient approach to assemble 1,2,3-triazole-fused 4 H -3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C-O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C-I bond was achieved by the use of Na 2CO 3in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.
Synthesis method of 1-iodo-alkyne compound
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Paragraph 0060-0063, (2021/01/24)
The invention discloses a synthetic method of a 1-iodo-alkyne compound. The preparation method comprises the following steps: in an aerobic environment, mixing terminal alkyne, soluble inorganic iodized salt, sodium phenylsulfinate or a derivative thereof
Copper-mediated conversion of alkynes into nitriles via iodotriazoles
Kori, Ryosuke,Murakami, Keigo,Nishiyama, Yoshitake,Toma, Tatsuya,Yokoshima, Satoshi
, p. 278 - 280 (2021/03/08)
We disclose our studies on a copper-mediated reaction of alkynes with trimethylsilyl azide to afford nitriles, and proposed a reaction mechanism, which involves an iodoalkyne and an iodotriazole as intermediates.
Au(I)-Catalyzed Hydration of 1-Iodoalkynes Leading to α-Iodoketones
Cazin, Catherine S. J.,Gómez-Herrera, Alberto,Hashim, Ishfaq Ibni,Nahra, Fady,Porré, Marre
supporting information, p. 6790 - 6794 (2020/11/23)
A catalytic protocol for the Au(I)-catalyzed hydration of 1-iodoalkynes is disclosed. The use of Au(I)–NHC catalyst enabled the straightforward synthesis of a variety of α-iodomethyl ketones in good to excellent yields. The utility of this simple method is further highlighted by showcasing iodination/hydration and hydration/oxidation sequential protocols leading to the construction of molecular complexity.
Chloramine Salt Mediated Oxidative Halogenation of Terminal Alkynes with KI or NaBr: Practical Synthesis of 1-Bromoalkynes and 1-Iodoalkynes
Liu, Xiaozu,Chen, Guojun,Li, Chenglong,Liu, Peijun
, p. 2051 - 2055 (2018/09/18)
A direct oxidative halogenation of terminal alkynes has been realized using chloramine-B as the oxidant and KI or NaBr as the halogen source. This reaction enables a general and practical access to synthetically valuable 1-bromoalkynes and 1-iodoalkynes i
Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(i) salt
Rao, Dodla S.,Reddy, Thurpu R.,Kashyap, Sudhir
supporting information, p. 1508 - 1518 (2018/03/08)
An efficient and highly chemoselective iodination of alkynes using a sulfonium iodate(i) electrophilc reagent under metal-free conditions has been realized. The reactivity of sulfonium iodate(i) salt could be significantly diverse in the presence of water
Sequential Functionalization of Alkynes and Alkenes Catalyzed by Gold(I) and Palladium(II) N-Heterocyclic Carbene Complexes
Gómez-Herrera, Alberto,Nahra, Fady,Brill, Marcel,Nolan, Steven P.,Cazin, Catherine S. J.
, p. 3381 - 3388 (2016/11/16)
The iodination of terminal alkynes for the synthesis of 1-iodoalkynes using N-iodosuccinimide in the presence of a AuI-NHC (NHC=N-heterocyclic carbene) catalyst is reported. A series of aromatic alkynes was transformed successfully into the corresponding 1-iodoalkynes in good to excellent yields under mild reaction conditions. The further use of these compounds as organic building blocks and the advantageous choice of metal-NHC complexes as catalysts for alkyne functionalization were further demonstrated by performing selective AuI-catalyzed hydrofluorination to yield (Z)-2-fluoro-1-iodoalkenes, followed by a Suzuki–Miyaura cross-coupling with aryl boronic acids catalyzed by a PdII-NHC complex to access trisubstituted (Z)-fluoroalkenes. All methodologies can be performed sequentially with only minor variations in the optimized individual reaction conditions, maintaining high efficiency and selectivity in all cases, which therefore, provides straightforward access to valuable fluorinated alkenes from commercially available terminal alkynes.
Dual gold-catalyzed head-to-tail coupling of iodoalkynes
Mader, Steffen,Molinari, Lise,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 3910 - 3913 (2015/10/19)
Various haloalkynes are converted in the presence of a dual activation gold catalyst. Via a dual activation process a completely atom economic head-totail coupling delivers gem-dihalogenated conjugated enynes as valuable building blocks for organic synthe
Halogen- and hydrogen-bonding triazole-functionalised porphyrin-based receptors for anion recognition
Gilday, Lydia C.,White, Nicholas G.,Beer, Paul D.
, p. 15766 - 15773 (2013/11/06)
Iodotriazole and triazole anion recognition groups have been integrated into a picket-fence zinc(ii)-metalloporphyrin scaffold to produce receptors for anion recognition and sensing applications. 1H NMR and UV/visible spectroscopic investigations reveal both host systems exhibit strong anion binding affinities in a range of solvent media. Importantly, the halogen-bonding iodotriazole-containing porphyrin-based host displays halide binding affinities substantially larger than the protic-functionalised analogue concomitant with a reduced strength of oxoanion complexation. This journal is The Royal Society of Chemistry 2013.
