1346939-35-2Relevant academic research and scientific papers
Directing Group-Promoted Inert C?O Bond Activation Using Versatile Boronic Acid as a Coupling Agent
Ambre, Ram,Wang, Ting-Hsuan,Xian, Anmei,Chen, Yu-Shiuan,Liang, Yu-Fu,Jurca, Titel,Zhao, Lili,Ong, Tiow-Gan
, p. 17021 - 17026 (2020/11/30)
A simple Ni(cod)2 and carbene mediated strategy facilitates the efficient catalytic cross-coupling of methoxyarenes with a variety of organoboron reagents. Directing groups facilitate the activation of inert C?O bonds in under-utilized aryl methyl ethers enabling their adaptation for C?C cross-coupling reactions as less toxic surrogates to the ubiquitous haloarenes. The method reported enables C?C cross-coupling with readily available and economical arylboronic acid reagents, which is unprecedented, and compares well with other organoboron reagents with similarly high reactivity. Extension to directing group assisted chemo-selective C?O bond cleavage, and further application towards the synthesis of novel bifunctionalized biaryls is reported. Key to the success of this protocol is the use of directing groups proximal to the reaction center to facilitate the activation of the inert C?OMe bond.
Microwave-Promoted ortho-C?H Bond (Hetero)arylation of Arylpyrimidines in Water Catalyzed by Ruthenium(II)?Carboxylate
Drev, Miha,Gro?elj, Uro?,Ledinek, Bine,Perdih, Franc,Svete, Jurij,?tefane, Bogdan,Po?gan, Franc
, p. 3824 - 3832 (2018/08/03)
Efficient diarylation of ortho-C?H bonds of 2-arylpyrimidines was achieved by Ru(II)?carboxylate-catalyzed reaction with aryl bromides in water, whereas meta-substituted phenylpyrimidines selectively led to monoarylation. The reaction is strongly accelerated under microwave irradiation, and is compatible with various functional groups on both coupling partners. As established from Hammett plots, electron-withdrawing groups on the pyrimidine substrates facilitate the arylation, while both, electron-withdrawing and electron-donating groups on the aryl bromides lead to a faster reaction. The C?H functionalization of 2-arylpyrimidines with heteroaryl halides provides potential multidentate ligands.
Cobalt-catalyzed C-H bond functionalizations with aryl and alkyl chlorides
Punji, Benudhar,Song, Weifeng,Shevchenko, Grigory A.,Ackermann, Lutz
supporting information, p. 10605 - 10610 (2013/08/23)
Inexpensive cobalt catalysts derived from N-heterocylic carbenes (NHC) allowed efficient catalytic C-H bond arylations on heteroaryl-substituted arenes with widely available aryl chlorides, which set the stage for the preparation of sterically hindered tr
Nickel-catalyzed Suzuki-Miyaura reaction of aryl fluorides
Tobisu, Mamoru,Xu, Tian,Shimasaki, Toshiaki,Chatani, Naoto
supporting information; experimental part, p. 19505 - 19511 (2012/01/31)
Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.
