154081-22-8Relevant academic research and scientific papers
Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV=O Catalysis
Nykaza, Trevor V.,Cooper, Julian C.,Li, Gen,Mahieu, Nolwenn,Ramirez, Antonio,Luzung, Michael R.,Radosevich, Alexander T.
supporting information, p. 15200 - 15205 (2018/11/30)
A main group-catalyzed method for the synthesis of aryl- and heteroarylamines by intermolecular C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermolecular coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) are demonstrated; the reaction is stereospecific with respect to Csp3-N bond formation. The method constitutes a new route from readily available building blocks to valuable nitrogen-containing products with complementarity in both scope and chemoselectivity to existing catalytic C-N coupling methods.
Copper(i)-catalyzed amidation reaction of organoboronic esters and isocyanates
Salim Lew, Tedrick Thomas,Wen Lim, Diane Shu,Zhang, Yugen
supporting information, p. 5140 - 5143 (2015/12/05)
A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using a ligand-free copper(i) catalyst. The reaction system demonstrated a broad substrate scope and provided convenient access to a wide variety of secondary amides.
Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement
Oda, Susumu,Yamamoto, Hisashi
supporting information, p. 8165 - 8168 (2013/08/23)
It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement. Copyright
New catalytic route to functionalized vinylboronates
Marciniec, Bogdan,Jankowska, Magdalena,Pietraszuk, Cezary
, p. 663 - 665 (2007/10/03)
Vinylsubstituted boronates i.e. vinyldioxaborolane and vinyldioxaborinane react regioselectively with olefins in the presence of RuHCl(CO)(PCy 3)2 with the formation of functionalized vinylboron derivatives. The reaction opens a new catalytic route for preparation of organoboranes. The Royal Society of Chemistry 2005.
Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes
Takahashi, Go,Shirakawa, Eiji,Tsuchimoto, Teruhisa,Kawakami, Yusuke
, p. 1459 - 1461 (2007/10/03)
Alkynes act not as substrates but as co-catalysts in the presence of a nickel catalyst, an organoboronate and an aldehyde to promote the addition reaction between the substrates in combination with H2O. The Royal Society of Chemistry 2005.
