87812-99-5Relevant articles and documents
Tetramethylammonium fluoride tetrahydrate-mediated transition metal-free coupling of aryl iodides with unactivated arenes in air
Nozawa-Kumada, Kanako,Nakamura, Kosuke,Kurosu, Satoshi,Iwakawa, Yuki,Denneval, Charline,Shigeno, Masanori,Kondo, Yoshinori
, p. 1042 - 1045 (2019/10/02)
Biaryls are important compounds with widespread applications in many fields. Tetramethylammonium fluoride tetrahydrate was found to promote the biaryl coupling of aryl iodides bearing electron-withdrawing substituents with unactivated arenes. The reaction takes place at temperatures between 100 and 150°C and can be applied to a wide range of aromatic and heteroaromatic rings, affording the products in moderate to high yields. The reaction does not require strong bases or expensive additives that are employed in the existing methods and can be conducted in air and moisture without any precautions.
Preparation method of 1-iododibenzofuran
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Paragraph 0022-0024; 0027-0029, (2019/08/03)
The invention provides a preparation method of 1-iododibenzofuran. The preparation method comprises the following steps: adding potassium tert-butoxide, dimethyl ether and cuprous iodide into a firstreactor, stirring the mixture under the protection of nitrogen gas, adding m-dinitrobenzene dissolved with pyridine into a system, then dissolving potassium tert-butoxide and o-iodophenol with dimethyl ether, adding the dissolved mixture into the system, fully reacting under the protection of the nitrogen gas, and separating to obtain 1-nitryldibenzofuran; then adding 1-nitryldibenzofuran into a second reactor, adding ethanol, water, iron powder and ammonium chloride, fully reacting, and separating to obtain 1-aminodibenzofuran; adding the 1-aminodibenzofuran into a third reactor, then addinghydrochloric acid, dropwise adding a sodium nitrite solution and a KI solution, fully reacting, and separating to obtain 1-iododibenzofuran. The preparation method has the beneficial effects of avoidance of carrying out the reactions under an ultralow temperature reaction condition, simple and feasible synthetic method, stable productivity, higher yield and low pollution, and has remarkable advantages on the aspect of batch production.
Photochemical nitration by tetranitromethane part XXX. Product isolation and identification in the photochemical reaction of dibenzofuran
Butts, Craig P.,Eberson, Lennart,Hartshorn, Michael P.,Robinson, Ward T.,Wood, Bryan R.
, p. 587 - 595 (2007/10/03)
The photolysis of the charge-transfer complex of dibenzofuran (1) and tetranitromethane in either dichloromethane or acetonitrile gives t-2-nitro-r-1-trinitromethyl-1,2-dihydrodibenzofuran (4), the epimeric 4-nitro-1-trinitromethyl-1,4-dihydrodibenzofurans 5 and 7, the epimeric 4-hydroxy-1-trinitromethyl-1,4-dihydrodibenzofurans 6 and 8, 3-trinitromethyldibenzofuran (13), and the four isomeric nitrodibenzofurans 9-12. The five adducts 4-8 are formed via attack by trinitromethanide ion at C1 of the dibenzofuran radical cation, while 3-trinitromethyldibenzofuran is formed by decomposition of an adduct, itself formed via initial attack of trinitromethanide ion at C3 of the dibenzofuran radical cation. The regiochemistry of attack of trinitromethanide ion on the radical cation of the non-alternant dibenzofuran system is in keeping with earlier theoretical predictions. In 1,1,1,3,3,3-hexafluoropropan-2-ol solution the analogous photolysis of the charge-transfer complex of dibenzofuran (1) and tetranitromethane gives only the four nitrodibenzofurans 9-12, the attack of trinitromethanide ion on the radical cation of dibenzofuran being suppressed by the solvent. X-Ray crystal structures are reported for compounds 4, 6 and 13, compound 6 representing the first hydroxytrinitromethyl adduct to be unambiguously assigned this structure. Acta Chemica Scandinavica 1996.
