4390-96-9Relevant academic research and scientific papers
Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of: N -(2-iodo-aryl) acrylamide
Dong, Kaiwu,Ren, Xinyi,Shen, Chaoren,Wang, Guangzhu
supporting information, p. 1135 - 1138 (2022/02/03)
A Ni/(S,S)-BDPP-catalyzed intramolecular Heck cyclization of N-(2-iodo-aryl) acrylamide with 2-methyl-2-phenylmalononitrile was developed to give oxindoles with good enantioselectivities. We found that utilizing such an electrophilic cyanation reagent cou
Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C-H Activation
Logeswaran, Ravichandran,Jeganmohan, Masilamani
supporting information, p. 5679 - 5683 (2021/08/03)
A novel chemodivergent cross-coupling of acrylamides and vinyl acetates has been realized via metal-catalyzed vinylic C-H activation. The selective olefinic C-H vinylation and alkenylation reaction was examined with a variety of differently functionalized acrylamides. The reaction efficiently generates a range of highly synthetically valuable butadienes with good functional group tolerance in good to moderate yields. A possible catalytic reaction mechanism involving the chelation-assisted olefinic C-H activation via an acetate-assisted deprotonation pathway is proposed.
Synthesis method and applications of N heteroatom polysubstituted benzoquaternary cycloketone
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Paragraph 0075-0080, (2020/03/12)
The invention discloses an N heteroatom polysubstituted benzoquaternary cycloketone synthesis method. According to the invention, the synthetic route starts from a known aniline compound A, the hundred g-scale preparation can be achieved, the yield can ac
Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions
Goh, Jeffrey,Loh, Teck-Peng,Maraswami, Manikantha
supporting information, p. 9724 - 9728 (2020/12/21)
Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.
Rh-Catalyzed asymmetric hydroaminomethylation of α-Substituted acrylamides: Application in the synthesis of RWAY
B?rner, Armin,Cunillera, Anton,Diéguez, Montserrat,Godard, Cyril,Lutz, Domke,Margalef, Jessica,Miró, Roger,Pamies, Oscar
supporting information, p. 9036 - 9040 (2020/11/30)
The successful rhodium-catalyzed asymmetric hydroformylation and hydroaminomethylation of α-substituted acrylamides is described using 1,3-phosphite-phosphoramidite ligands based on a sugar backbone. A broad scope of chiral aldehydes and amines were afforded in high yields and excellent enantioselectivities (up to 99%). Furthermore, the synthetic potential of this method is demonstrated by the single-step synthesis of the brain imaging molecule RWAY.
Domino Carbopalladation/C-H Activation as a Quick Access to Polycyclic Frameworks
Saha, Nemai,Wang, Haiwen,Zhang, Shengyi,Du, Yongliang,Zhu, Daqian,Hu, Yumin,Huang, Peng,Wen, Shijun
supporting information, p. 712 - 715 (2018/02/09)
A new type of domino reaction for synthesis of heterocycles fusing the important bioactive cores, such as oxindole, indoline, and isoquinoline, is presented. Upon exposure to the very common palladium catalyst, the conceptually designed N-alkenyl iodobiaryls undergo a sequential carbopalladation/C-H activation to build polycyclic frameworks. These novel unique frameworks may provide structure sources in fragment-based drug discovery.
A tethering directing group strategy for ruthenium-catalyzed intramolecular alkene hydroarylation
Kilaru, Praveen,Acharya, Sunil P.,Zhao, Pinjing
supporting information, p. 924 - 927 (2018/02/07)
We report a new catalyst design for N-heterocycle synthesis that utilizes an alkene-tethered amide moiety as a directing group for aromatic C-H activation. This tethering directing group strategy is demonstrated in a ruthenium-catalyzed intramolecular alk
Transformable Sulfoximine Assisted One-Pot Double Annulation of Vinylic C-H Bonds with Unactivated Alkynes
Shankar, Majji,Guntreddi, Tirumaleswararao,Ramesh,Sahoo, Akhila K.
supporting information, p. 5665 - 5668 (2017/10/25)
The methylphenyl sulfoximine (MPS) directing group (DG) successfully promotes the one-pot double annulation of acrylic acids with alkynes under Ru catalysis, which is unprecedented. Diverse arrays of pyrido-fused-isoquinolinone skeletons are fabricated from acrylamides, creating two C-C and two C-N bonds in a single operation. The unsymmetrical annulation with two distinct alkynes is presented. The recovery of methylphenyl sulfoxide, a precursor of MPS, validates the synthetic adaptability of transformable-DG (TfDG) in C-H activation.
High-valent palladium-promoted formal Wagner-Meerwein rearrangement
Wu, Hongmiao,Yang, Bin,Zhu, Lin,Lu, Ronghua,Li, Guigen,Lu, Hongjian
supporting information, p. 5804 - 5807 (2016/11/29)
An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolidine-2,4-diones and oxazolidin-2-ones. The reaction has a broad substrate scope in which both aryl and alkyl groups can be utilized as efficient migrating groups. Experimental evidence suggests that the reaction is initiated by anti-oxy-palladation of the olefin, followed by oxidative generation of an alkyl PdIV intermediate and a concerted migration-fluorination.
Intramolecular Paterno-Buechi reaction of atropisomeric α-oxoamides in solution and in the solid-state
Raghunathan, Ramya,Kumarasamy, Elango,Iyer, Akila,Ugrinov, Angel,Sivaguru
supporting information, p. 8713 - 8715 (2013/09/23)
Atropisomeric α-oxoamides were synthesized and employed for intramolecular Paterno-Buechi reaction leading to very high enantio- and diastereoselectivity in the bicyclic oxetane photoproduct. A reversal of product selectivity was observed in solution and in the solid-state.
