21315-63-9Relevant academic research and scientific papers
Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines
D'Amaral, Melissa C.,Jamkhou, Nick,Adler, Marc J.
supporting information, p. 288 - 295 (2021/01/28)
A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is
Tandem Synthesis of 2-Carboxybenzofurans via Sequential Cu-Catalyzed C-O Coupling and Mo(CO)6-Mediated Carbonylation Reactions
Mo, Qinliang,Sun, Nan,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 11490 - 11500 (2020/10/12)
A modular tandem synthesis of 2-carboxybenzofurans from 2-gem-dibromovinylphenols has been established based on a sequence of Cu-catalyzed intramolecular C-O coupling and Mo(CO)6-mediated intermolecular carbonylation reactions. This protocol allowed one-step access to a broad variety of functionalized benzofuran-2-carboxylic acids, esters, and amides in good to excellent yields under Pd- and CO gas-free conditions.
Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds between Aromatic Acids and Amines
Movahed, Farzaneh Soleymani,Sawant, Dinesh N.,Bagal, Dattatraya B.,Saito, Susumu
, p. 3253 - 3262 (2020/11/02)
The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using 31 P NMR spectroscopy and ESI mass spectrometry.
Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines
Sawant, Dinesh N.,Bagal, Dattatraya B.,Ogawa, Saeko,Selvam, Kaliyamoorthy,Saito, Susumu
supporting information, p. 4397 - 4400 (2018/08/09)
Tetrakis(dimethylamido)diboron and tetrahydroxydiboron are herein reported as new catalysts for the synthesis of aryl amides by catalytic condensation of aromatic carboxylic acids with amines. The developed protocol is both simple and highly efficient over a broad range of substrates. This method thus represents an attractive approach for the use of diboron catalysts in the synthesis of amides without having to resort to stoichiometric or additional dehydrating agents.
Facile preparation of amides from carboxylic acids and amines with ion-supported Ph3P
Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
, p. 3971 - 3977 (2013/06/27)
Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide (IS-Ph3P), could be used for the facile amidation of a wide range of carboxylic acids with amines in the presence of bromotrichloromethane to provide the corresponding amides in good yields. In the present reaction, the desired amides were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether or chloroform and subsequent removal of the solvent from the extract. Moreover, ion-supported Ph3PO (IS-Ph3PO), which was a co-product derived from IS-Ph3P in the present reductive condensation, was recovered in high yield and could be reduced to IS-Ph3P for reuse in the same amidation of carboxylic acid.
Radical dearomatising spirocyclisations onto the C-2 position of benzofuran and indole
Kyei, Afua S.,Tchabanenko, Kirill,Baldwin, Jack E.,Adlington, Robert M.
, p. 8931 - 8934 (2007/10/03)
New spirolactams were obtained in radical dearomatising spirocyclisations of alkyl, vinyl and aryl radicals tethered at the C-2 positions of benzofuran and indole. Spirolactams were obtained via an intramolecular radical ipso-type spirocyclisation in benzofuran and indole systems. Alkyl, vinyl and aryl radicals, tethered at the C-2 position of the heterocycle underwent radical cyclisation to produce novel tricyclic partially dearomatised heterocycles in moderate yields. Fragmentation of the furan ring was observed subsequent to spirocyclisation of a vinyl radical onto a benzofuran.
