144765-53-7Relevant articles and documents
Visible light photoredox catalysed amidation of carboxylic acids with amines
Srivastava, Vishal,Singh, Pravin K.,Singh, Praveen P.
, p. 40 - 43 (2019)
A visible-light promoted photoredox catalysed, green one-pot approach for the amidation of carboxylic acids with amines has been developed for the synthesis of diverse aliphatic and aromatic amides. The proposed strategy is extendable also to biologically active amides and could represent a low-cost alternative to the common synthetic pathways. The developed strategy may hold great potential for a comprehensive display of biologically interesting peptide synthesis and amino acid modification.
Unique physicochemical and catalytic properties dictated by the B3NO2 ring system
Noda, Hidetoshi,Furutachi, Makoto,Asada, Yasuko,Shibasaki, Masakatsu,Kumagai, Naoya
, p. 571 - 577 (2017/06/01)
The expansion of molecular diversity beyond what nature can produce is a fundamental objective in chemical sciences. Despite the rich chemistry of boron-containing heterocycles, the 1,3-dioxa-5-aza-2,4,6-triborinane (DATB) ring system, which is characterized by a six-membered B3NO2 core, remains elusive. Here, we report the synthesis of m-terphenyl-templated DATB derivatives, displaying high stability and peculiar Lewis acidity arising from the three suitably arranged boron atoms. We identify a particular utility for DATB in the dehydrative amidation of carboxylic acids and amines, a reaction of high academic and industrial importance. The three boron sites are proposed to engage in substrate assembly, lowering the entropic cost of the transition state, in contrast with the operative mechanism of previously reported catalysts and amide coupling reagents. The distinct mechanistic pathway dictated by the DATB core will advance not only such amidations, but also other reactions driven by multisite activation.
Direct Coupling of Functionalized Organolithium Compounds with Aryl and Vinyl Halides
Barluenga, Jose,Montserrat, Javier M.,Florez, Josefa
, p. 5976 - 5980 (2007/10/02)
The reaction between β- and γ-nitrogen-functionalized and γ- and ε-oxygen-functionalized organolithium compounds 3, 4, 30-32 and different aromatic, heteroaromatic, and vinylic halides affords directly the corresponding substitution products: functionalized benzamides 5-26 and alcohols 33-37.Symmetrical and mixed products of double coupling 38-40 were also prepared from 1,4-diiodobenzene.The formation of alkyl halides as intermediates has been verified.Aryl or vinyl halides giving rise to unstable aryl or vinyllithium reagents were unsuccessful in the coupling reaction.
