120870-46-4Relevant academic research and scientific papers
Divergent Syntheses of (Z)-3-Alkylideneisobenzofuran-1(3 H)-ones and 1 H-Isochromen-1-ones by Copper-Catalyzed Cycloisomerization of 2-Alkynylbenzoic Acids in Ionic Liquids
Mancuso, Raffaella,Pomelli, Christian S.,Chiappetta, Piera,Gioia, Katia F.,Maner, Asif,Marino, Nadia,Veltri, Lucia,Chiappe, Cinzia,Gabriele, Bartolo
, p. 6673 - 6680 (2018/06/01)
The cycloisomerization of readily available 2-alkynylbenzoic acids 1 in ionic liquids (ILs) as recyclable reaction media has been studied under the catalytic action of CuCl2. With substrates bearing an aryl group on the triple bond, a mixture o
Stoichiometric and Catalytic C?C and C?H Bond Formation with B(C6F5)3 via Cationic Intermediates
Soltani, Yashar,Wilkins, Lewis C.,Melen, Rebecca L.
, p. 11995 - 11999 (2017/09/20)
This work showcases a new catalytic cyclization reaction using a highly Lewis acidic borane with concomitant C?H or C?C bond formation. The activation of alkyne-containing substrates with B(C6F5)3 enabled the first catalytic intramolecular cyclizations of carboxylic acid substrates using this Lewis acid. In addition, intramolecular cyclizations of esters enable C?C bond formation as catalytic B(C6F5)3 can be used to effect formal 1,5-alkyl migrations from the ester functional groups to unsaturated carbon–carbon frameworks. This metal-free method was used for the catalytic formation of complex dihydropyrones and isocoumarins in very good yields under relatively mild conditions with excellent atom efficiency.
Divergent syntheses of iodinated isobenzofuranones and isochromenones by iodolactonization of 2-alkynylbenzoic acids in ionic liquids
Mancuso, Raffaella,Pomelli, Christian C.,Malafronte, Francesco,Maner, Asif,Marino, Nadia,Chiappe, Cinzia,Gabriele, Bartolo
, p. 4831 - 4841 (2017/07/10)
The regiochemical outcome of the iodolactonization of 2-alkynylbenzoic acids, carried out at 100 °C in ionic liquids (ILs) as unconventional solvents and with molecular iodine as the iodine source, in the absence of external bases, was found to be strongl
PhI(OCOCF3)2-Mediated Cyclization of o -(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione
Yang, Chao,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 5320 - 5328 (2015/05/27)
The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl)benzamides in MeCN/H2O, mediated by metal-free, h
Synthesis of isocoumarins: Rhenium complex-catalyzed cyclization of 2-ethynylbenzoic acids
Umeda, Rui,Yoshikawa, Shunya,Yamashita, Kouji,Nishiyama, Yutaka
, p. 2172 - 2179 (2015/12/12)
When 2-ethynylbenzoic acids were treated with a catalytic amount of a rhenium complex, such as ReCl(CO)5, 6-endo cyclization of 2-ethynylbenzoic acids proceeded with a high selectivity to give the corresponding isocoumarins in moderate to good yields.
Cu(II)-mediated ortho C-H alkynylation of (hetero)arenes with terminal alkynes
Shang, Ming,Wang, Hong-Li,Sun, Shang-Zheng,Dai, Hui-Xiong,Yu, Jin-Quan
, p. 11590 - 11593 (2014/10/15)
Cu(II)-promoted ortho alkynylation of arenes and heteroarenes with terminal alkynes has been developed to prepare aryl alkynes. A variety of arenes and terminal alkynes bearing different substituents are compatible with this reaction, thus providing an alternative disconnection to Sonogashira coupling.
On homogeneous gold/palladium catalytic systems
Hashmi, A. Stephen K.,Lothschuetz, Christian,Doepp, Rene,Ackermann, Martin,De Buck Becker, Janosc,Rudolph, Matthias,Scholz, Christian,Rominger, Frank
, p. 133 - 147 (2012/04/10)
Two substrates containing an aryl iodide and an allenoate ester were prepared and the goldinduced cycloisomerisation to vinylgold(I) species and their proto-deauration as well as the intramolecular palladium-catalysed cross-coupling reactions were investigated. Switching to catalytic amounts of gold and palladium and stoichiometric amounts of silver did indeed furnish the product of a cycloisomerisation/ intramolecular cross-coupling. Control experiments revealed that silver cannot substitute for gold or palladium in these reactions, but a different palladium catalyst in a different oxidation state also afforded the cycloisomerisation/intramolecular crosscoupling products in only slightly reduced yields. By ICP analysis the palladium was shown to contain gold only at the sub-ppm level. This shows how carefully results obtained with such systems have to be interpreted. Then a series of allylic and benzylic o-alkynylbenzoates were investigated in gold-and palladium-catalysed reactions. For esters of benzyl alcohol and cinnamyl alcohol no palladium co-catalyst was needed for the conversion. All reagents were thoroughly checked for palladium traces by ICP analysis in order to thoroughly exclude a gold/palladium cocatalysis. Optimisation of the gold complex, counter ion and solvent showed that gold(I) isonitrile precatalysts and silver triflate as activator in dioxane are suitable to convert a number of substrates with aryl, alkyl and even cyclopropyl substituents. Crossover experiments proved an intermolecular allyl transfer.
Transmission of Polar Effects. Part 21. Alkaline Hydrolysis of the 2'- and 4'-substituted 2-Methoxycarbonyldiphenylacetylenes and (Z)-2'- and -4'- Substituted 2-Methoxycarbonylstilbenes and the Ionisation and Esterification, with Diazodiphenylmethane of t
Bowden, Keith,Ghadir, Khalaf D. F.
, p. 1333 - 1338 (2007/10/02)
The rate coefficients for the alkaline hydrolysis of a series of 2'- and 4'-substituted 2-methoxycarbonyldiphenylacetylenes and (Z)-2-methoxycarbonylstilbenes have been determined in 70percent (v/v) dimethyl sulphoxide-water at both 30.0 and 50.0 deg C an
