Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

Li, Yuxiu; Wang, Kuai; Ping, Yuanyuan; Wang, Yifan; Kong, Wangqing

doi:10.1021/acs.orglett.7b03713

Cited by 77 publications

(46 citation statements)

References 92 publications

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“…In 2018, the Kong group used arylboronic acids as the terminal reagents in a nickel‐catalyzed intramolecular diarylation of alkenes to access 3,3‐disubstituted oxindoles (Scheme 61). [ 131 ] A wide range of electrophiles, such as aryl halides (X = Cl, Br, I) and triflates were compatible with the reaction conditions. Notably, the inexpensive and unreactive aryl esters were also suitable substrates with good yields, providing an alternative method to the conventional palladium‐catalyzed analogues.…”

Section: Intramolecular Dicarbofunctionalization Of Alkenes Via Cyclimentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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As a straightforward strategy for rapidly increasing molecular complexity, dicarbofunctionalization of alkenes has attracted substantial interests of organic synthesis, medicine chemistry, and materials science. Nickel-catalyzed cascade dicarbofunctionalizations have been flourished in this area recently, and nickel-mediated radical pathways particularly offer new opportunities in conjunctive cross-couplings with alkyl coupling partners. Herein, we give a comprehensive review of nickel-catalyzed dicarbofunctionalization of alkenes through a historical perspective, including intermolecular three-component reactions and intramolecular cascade reactions. Among the pathways discussed in this review, the carbometallation/cross-coupling process and the radical addition/cross-coupling process are the two major pathways for the nickel-catalyzed dicarbofunctionalization of alkenes. The oxidative cyclization and 1,2-metallate shift processes are also selectively discussed. These methods overcome the limitations associated with the reactions using noble metals in the field, providing an efficient and straightforward access to structurally diversified molecules. Yun-Cheng Luo (right) received his BSc degree in 2016 and master degree in 2019 from University of Science and Technology of China. Then he joined Professor Xingang Zhang's group at Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences to pursue his doctorate in organic chemistry. His research interests are focused on the activation of inert C-H or C-X bonds of bulky chemicals and their applications in the synthesis of fluorine-containing compounds. Chang Xu (middle) obtained his BSc degree in basic pharmacy from China Pharmaceutical University (China) in 2015. With an interest in organic chemistry and medicinal chemistry, he then began his graduate studies at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences under the supervision of Professor Xingang Zhang. His research interests are focused on the activation and transformations of fluoroalkylanes and their applications in medicinal chemistry. Xingang Zhang (left) obtained his BSc degree in 1998 from Sichuan University (China) and received the Ph.D. in 2003 at Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. After his postdoctoral work at University of Illinois at Urbana Champaign (USA), he joined the faculty team of SIOC as a research associate professor in 2008, and became research professor in 2012. His current research interests are focused on organofluorine chemistry and chemical biology.

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Section: Intramolecular Dicarbofunctionalization Of Alkenes Via Cyclimentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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“…In most cases, the coupling reactions occur in the presence of palladium as a catalyst [8]. Other metals are also used to catalyze the Heck reaction, for example, nickel having many advantages being abundant, non-toxic, and cost effective [9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

et al. 2020

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Magnetic particles were prepared by a hydrothermal method and then successively covered by Metal-Organic-Frameworks MIL-101-NH 2 with a high surface area. This was followed by deposition of Pd(OAc) 2 on Fe 3 O 4-NH 2 @MIL-101-NH 2 particles. The final catalyst was characterized with FT-IR, nitrogen physisorption, thermogravimetry (TGA), scanning electron microscopy (SEM) combined with energy dispersive X-ray analysis (EDX), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), wide-angle X-ray diffraction spectroscopy (XRD) and X-ray photoelectron spectroscopy (XPS). The prepared magnetic catalyst was effectively used in the Heck coupling reaction in the presence of an inorganic base. The reaction parameters such as the base type, amounts of catalyst and solvents, temperature, and substrates ratios were optimized. The catalyst was then magnetically separated, washed, and reused 7 times without losing significantly catalytic activity.

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“…[12] In the beginning, reacting 1 a (0.2 mmol) with 2 a (0.26 mmol) by using Pd(OAc) 2 (10 mol %) as a catalyst, PCy 3 (20 mol %) as a ligand, and K 2 CO 3 as a base under an argon atmosphere in MeCN at 80°C led to the formation of the desired 3-phosphinomethyl 3,3-disubstituted oxindole 3 a in 18% yield ( Table 1, entry 1). Among many different approaches to 3,3'-disubstituted oxindoles, palladiumcatalyzed oxidative difunctionalization alkenes in Narylacrylamides provides direct and potentially more efficient access to oxindoles.…”

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“…(Table 1, entry 5). Subsequently, we checked the effect of various bases and found that a serious decrease in the yield was observed using Cs 2 CO 3 , K 3 PO 4 and Et 3 N, indicating that the choice of base was also crucial for the reaction ( Table 1, entries [10][11][12]. Subsequently, we checked the effect of various bases and found that a serious decrease in the yield was observed using Cs 2 CO 3 , K 3 PO 4 and Et 3 N, indicating that the choice of base was also crucial for the reaction ( Table 1, entries [10][11][12].…”

mentioning

confidence: 99%

“…Among many different approaches to 3,3'-disubstituted oxindoles, palladiumcatalyzed oxidative difunctionalization alkenes in Narylacrylamides provides direct and potentially more efficient access to oxindoles. [12] In the beginning, reacting 1 a (0.2 mmol) with 2 a (0.26 mmol) by using Pd(OAc) 2 (10 mol %) as a catalyst, PCy 3 (20 mol %) as a ligand, and K 2 CO 3 as a base under an argon atmosphere in MeCN at 80°C led to the formation of the desired 3-phosphinomethyl 3,3-disubstituted oxindole 3 a in 18% yield ( Table 1, entry 1).…”

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confidence: 99%

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Palladium‐Catalyzed Domino Heck/Phosphorylation towards 3,3‐Disubstituted Phosphinonyloxindoles

Huangfu

et al. 2019

Adv Synth Catal

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The first Pd-catalyzed domino Heck/ phosphorylation of N-(2-iodophenyl)acrylamides with secondary phosphine oxides has been developed. The use of PdCl 2 as a catalyst, 1,4-bis (diphenylphosphino)butane as a ligand, K 2 CO 3 as a base, various N-(2-iodophenyl)acrylamide derivatives are tolerant in this transformation, affording 3phosphinomethyl 3,3-disubstituted oxindole products in good to excellent yields. This transformation offers a straightforward route to the formation of the new CÀ C and PÀ C bonds, oxindole ring in one step. Moreover, this method can be easily adapted to large-scale preparation. Scheme 1. The route to oxindole-based phosphine oxides.

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Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

Cited by 77 publications

References 92 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

Palladium‐Catalyzed Domino Heck/Phosphorylation towards 3,3‐Disubstituted Phosphinonyloxindoles

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Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

Cited by 77 publications

References 92 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

Palladium‐Catalyzed Domino Heck/Phosphorylation towards 3,3‐Disubstituted Phosphinonyloxindoles

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Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†