13234-79-2Relevant academic research and scientific papers
A new approach to the solid-phase Suzuki coupling reaction
Piettre, Serge R.,Baltzer, Sylvie
, p. 1197 - 1200 (1997)
Treatment of polymer-bound aryl halides with pinacol ester of diboron under palladium (0) catalysis gave the corresponding polymer-bound boronates. The Suzuki coupling reaction was then carried out using a variety of aryl halides. Cleavage from the solid support delivered the expected products in usually good yields and high purity.
Preparation method of acrylamido
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Paragraph 0118; 0135-0140, (2022/01/04)
The present invention relates to a method for preparing a pyrimidine, 9-fluorenone as raw material, by open loop, acid chloride, amidation, chlorination, Hofmann (Hofmann) rearrangement degradation to give 2-(4'-chlorophenyl) aniline, and then condensed with 2-chloronicotinamide to give the product acetoimide, the present invention also relates accordingly to the intermediates 4'-chloro-2-bibenzamide and 4'-chloro-2-aminobiphenyl preparation method. The method of the present invention can obtain the target product with high yield, high purity, and can reduce costs while reducing environmental harm.
Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation
Zhang, Zhiguo,Li, Xiang,Song, Mengmeng,Wan, Yameng,Zheng, Dan,Zhang, Guisheng,Chen, Gong
, p. 12792 - 12799 (2019/07/03)
8-Aminoquinoline (AQ) is a widely used bidentate auxiliary in metal-catalyzed directed C-H functionalization reactions. Herein, we report an efficient and chemoselective method to convert various N-quinolyl carboxamides to primary amides with the treatment of a stoichiometric amount of 2-iodoxybenzoic acid oxidant or the combination of a catalytic amount of 2-iodobenzoic acid and Oxone co-oxidant in mixed solvents of H2O and HFIP. Its unique compatibility with the Phth-protected α-amino acid (αAA) substrates enhances the overall synthetic utility of the AQ-directed palladium-catalyzed C-H functionalization strategy for synthesis of complex αAAs.
Activation of nitriles by silver(I) N-heterocyclic carbenes: An efficient on-water synthesis of primary amides
Thirukovela, Narasimha Swamy,Balaboina, Ramesh,Kankala, Shravankumar,Vadde, Ravindhar,Vasam, Chandra Sekhar
supporting information, p. 2637 - 2641 (2019/03/21)
A first example of silver(I) N-heterocyclic carbene (Ag(I)-NHC) catalyzed on-water synthesis of primary amides by hydration of nitriles under mild reaction conditions is described. This organometallic catalytic system has excellent tolerance for various homo-aromatic, hetero-aromatic and aliphatic nitriles to afford primary amides in good yields in neat water.
Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
Wu, Youzhi,Sun, Peng,Zhang, Kaifan,Yang, Tie,Yao, Hequan,Lin, Aijun
, p. 2166 - 2173 (2016/03/15)
Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.
Novel syntheses of fluorenones via nitrile-directed palladium-catalyzed C-H and dual C-H bond activation
Wan, Jung-Chih,Huang, Jun-Min,Jhan, Yu-Huei,Hsieh, Jen-Chieh
, p. 2742 - 2745 (2013/07/19)
Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.
Combining transition metal catalysis with radical chemistry: Dramatic acceleration of palladium-catalyzed C-H arylation with diaryliodonium salts
Neufeldt, Sharon R.,Sanford, Melanie S.
, p. 3517 - 3522 (2013/02/22)
This paper describes a photoredox palladium/iridium-catalyzed C-H arylation with diaryliodonium reagents. Details of the reaction optimization, substrate scope, and mechanism are presented along with a comparison to a related method in which aryldiazonium salts are used in place of diaryliodonium reagents. The unprecedentedly mild reaction conditions (25 C in methanol), the requirement for light and a photocatalyst, the inhibitory effect of radical scavengers, and the observed chemoselectivity trends are all consistent with a radical-mediated mechanism for this transformation. This stands in contrast to the analogous thermal reaction with diaryliodonium reagents that is believed to proceed via an ionic' 2e- pathway and requires a much higher reaction temperature (100 C).
A simple and efficient approach for the palladium-catalyzed ligand-free Suzuki reaction in water
Liu, Chun,Zhang, Yixia,Liu, Ning,Qiu, Jieshan
supporting information, p. 2999 - 3003,5 (2020/09/16)
A general and efficient protocol is described for the palladium-catalyzed ligand-free and aerobic Suzuki reaction in water in the absence of any additive. The results demonstrate that the base played a crucial role in the high efficiency. The Pd(OAc)2/(i-Pr)2NH/H2O system showed the highest catalytic activity towards the Suzuki reaction of a wide range of aryl halides bearing hydrophilic or hydrophobic groups.
Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine
Naredla, Rajasekhar Reddy,Klumpp, Douglas A.
experimental part, p. 4779 - 4781 (2012/09/07)
Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.
Palladium-catalyzed ortho-arylation of benzamides via direct sp2 C-H bond activation
Li, Dan-Dan,Yuan, Ting-Ting,Wang, Guan-Wu
experimental part, p. 3341 - 3347 (2012/05/20)
The palladium-catalyzed ortho-arylation of benzamides by aryl iodides has been demonstrated with the simplest amide CONH2 as a directing group for the first time. This protocol can be applied to various benzamides and aryl iodides with both electron-donating and electron-withdrawing groups. In addition, the synthesized biphenyl-2-carboxamides can be further transformed to other biphenyl derivatives such as nitriles, carboxylic acids, carbamates, and amines.
