146448-53-5Relevant academic research and scientific papers
Ruthenium-Catalyzed Addition of Aromatic Amides to Internal Alkynes and Subsequent Intramolecular Cyclization for the Atom-Economical Synthesis of Isoindolinones
Miura, Hiroki,Terajima, Sachie,Tsutsui, Kentaro,Shishido, Tetsuya
, p. 1231 - 1239 (2017)
A selective and atom-economical synthesis of isoindolinones is described. This novel synthetic strategy involves two catalytic reactions: the ruthenium-catalyzed regioselective alkenylation of aromatic C-H bond of aromatic amides with internal alkynes, an
Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
Tóth, Balázs L.,Sályi, Gerg?,Domján, Attila,Egyed, Orsolya,Bényei, Attila,Gonda, Zsombor,Novák, Zoltán
supporting information, p. 348 - 354 (2021/11/09)
The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols
Kumar, Shreemoyee,Nair, Akshay M.,Volla, Chandra M. R.
, p. 6280 - 6283 (2021/07/02)
We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is
Ruthenium-Catalyzed Synthesis of Isoindolinones via Amide-Directed Addition of Aromatic C-H Bonds to Aldimines
Miura, Hiroki,Kimura, Yuriko,Terajima, Sachie,Shishido, Tetsuya
supporting information, p. 2807 - 2811 (2019/02/01)
Ruthenium-catalyzed addition of aromatic C-H bonds to aldimines is described. [RuCl2(p-cymene)]2 functions as an efficient catalyst to promote the coupling of aryl amides with aldimines in the presence of a catalytic amount of base to give the corresponding isoindolinone derivatives. The nature of the substituent at the N-atom of the amides is crucial for the efficient conversion of the substrates, and a p-toluenesulfonyl group is the functionality of choice. A variety of amides and aldimines participated in the present Ru-catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield.
Controllable construction of isoquinolinedione and isocoumarin scaffolds: Via RhIII-catalyzed C-H annulation of N -tosylbenzamides with diazo compounds
Liu, Yanfei,Wu, Jiaping,Qian, Baiyang,Shang, Yongjia
supporting information, p. 8768 - 8777 (2019/10/16)
A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.
Improvements of C-H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics
Babin, Victor,Benoist, Florian,Bouillon, Jean-Philippe,Cailly, Thomas,Dubost, Emmanuelle,Fabis, Frédéric,Hébert, Alexandra,Pigrée, Gilbert
, p. 4393 - 4400 (2019/11/21)
An improved protocol to perform C-H radio-iodination is described. These new conditions allow rapid and clean formation of radio-iodinated N-acylsulfonamides using [125 I]NIS and catalytic amounts of palladium acetate and para-toluenesulfonic a
N-Sulfonyl acetylketenimine as a highly reactive intermediate for synthesis of N-Aroylsulfonamides
Yang, Weiguang,Huang, Dayun,Zeng, Xiaobao,Zhang, Jianlan,Wang, Xinyan,Hu, Yuefei
, p. 381 - 386 (2018/12/13)
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement.
Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant
Youn, So Won,Ko, Tae Yun,Kim, Young Ho,Kim, Yun Ah
supporting information, p. 7869 - 7874 (2019/01/14)
Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C-C/C-N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.
Palladium-Mediated Site-Selective C-H Radio-iodination
Dubost, Emmanuelle,Babin, Victor,Benoist, Florian,Hébert, Alexandra,Barbey, Pierre,Chollet, Céline,Bouillon, Jean-Philippe,Manrique, Alain,Pieters, Grégory,Fabis, Frédéric,Cailly, Thomas
supporting information, p. 6302 - 6305 (2018/10/02)
The palladium-mediated C-H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.
Co-Catalyzed Synthesis of N-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides
Fang, Yue,Gu, Zheng-Yang,Wang, Shun-Yi,Yang, Jin-Ming,Ji, Shun-Jun
, p. 9364 - 9369 (2018/07/09)
A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.
