613-46-7Relevant articles and documents
Photocycloaddition of Cyanonaphthalenes to 1,3-Cyclohexadiene
Noh, Taehee,Kim, Daekyun,Kim, Yong-Jae
, p. 1212 - 1216 (1998)
To prevent secondary processes due to facile thermal reaction, low-temperature irradiations of cyanonaphthalenes and 1,3-cyclohexadiene through a Pyrex filter were conducted. Along with the identification of the products, the results of the triplet-sensitized photoreaction of the irradiated mixture, low-temperature 1H NMR study of the irradiated mixture, and the Cope rearrangement reaction of some products suggested that the primary major products are the corresponding exo-[4 + 4] adducts fused at 1,4 position of the naphthalene skeleton and the syn-[2 + 2] adducts fused at 1,2 position. The formations of the primary products in these singlet-state photocycloaddition reactions were interpreted by primary and secondary orbital interactions. A rationalization for the previous results on the photoreactions at room temperature was also provided.
Juchnovski et al.
, p. 1271,1277 (1970)
McCullough,Wu
, p. 1136 (1972)
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Goldstein,Chastellain
, p. 1481,1482, 1484, 1485 (1934)
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Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones
Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki
supporting information, p. 3799 - 3802 (2022/04/07)
The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.
Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis
De Jesus Silva, Jordan,Bartalucci, Niccolò,Jelier, Benson,Grosslight, Samantha,Gensch, Tobias,Schünemann, Claas,Müller, Bernd,Kamer, Paul C. J.,Copéret, Christophe,Sigman, Matthew S.,Togni, Antonio
, (2021/11/10)
A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.
CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source
Ren, Yun-Lai,Shen, Zhenpeng,Tian, Xinzhe,Xing, Ai-Ping,Zhao, Zhe
, (2020/10/26)
Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.
