One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids

Mphahlele, Malose J.; Mphahlele, Mamasegare Mabel

doi:10.3390/molecules15107423

Cited by 11 publications

(10 citation statements)

References 31 publications

(37 reference statements)

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“…Selective coupling at a CI bond in the presence of a CCl bond was also illustrated by Mphahlele and Mtshemia130,131 who synthesized compounds 392 in 53–60% yield from 2‐aryl‐4‐chloro‐3‐iodoquinolines 391 and phenylboronic acid (Scheme ).…”

Section: Cross‐coupling Reactions Of Polyhalogenated Six‐membered Hmentioning

confidence: 79%

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2012

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The palladium-catalyzed Suzuki-Miyaura reaction of multiply halogenated, electron-rich and electron-deficient heteroarenes is one of the most reliable and environmentally friendly tools for installing a wide range of non-functionalized and functionalized carbon substituents onto heteroaromatic systems with exquisite chemo-and site-selectivity. For substrates with different halogen groups the chemoselectivity of the Suzuki-Miyaura reactions has been found to be dependent on the reactivity difference between the halogens. However, the hardest achievement of selectivity in Suzuki-Miyaura monocouplings involving polyhalogenated heteroarenes with identical halogen atoms has been shown to be dominated by steric and electronic effects and the presence of directing groups at positions neighbouring the reaction sites. Moreover, in the case of symmetrically substituted dihaloheteroarenes with identical halogen atoms, highly selective monocoupling reactions have often been achieved only after a careful optimization of reaction parameters including the catalyst precursor, base, solvent, and the molar ratio between electrophile and organoboron reagent. This critical review with 341 references covers developments on the chemo-and site-selective Suzuki-Miyaura monocoupling reactions of polyhalogenated heteroarenes with different or identical halogen atoms. It also includes the synthesis of polysubstituted heteroarenes, not easily accessible by other means, via consecutive monocoupling reactions and/ or a more synthetically valuable approach involving one-pot polycoupling reactions.

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Section: Cross‐coupling Reactions Of Polyhalogenated Six‐membered Hmentioning

confidence: 79%

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2012

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“…The synthesis and analytical data of compounds 1a-d have been described previously. 25 Suzuki-Miyaura cross-coupling of 1 with arylboronic acids; general procedure 2-Aryl-4-chloroquinoline 1 (1 equiv. ), arylboronic acid (1.2 equiv.…”

Section: Methodsmentioning

confidence: 99%

2,4-Diarylquinolines: Synthesis, Absorption and Emission Properties

Adeloye

Mphahlele

2014

Journal of Chemical Research

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“…Suzuki cross‐coupling of the 2‐aryl‐4‐chloro‐3‐iodoquinolines 43 with arylboronic acids (1.2–2.0 equiv) using Pd(PPh 3 ) 4 as a catalyst and 2 M K 2 CO 3 in DMF under reflux afforded the 2,3‐diaryl‐4‐chloroquinolines 74 in moderate yields (Scheme 28) [69, 70]. The corresponding 2‐aryl‐3‐iodo‐4‐methoxyquinolines afforded the 2,3‐diaryl‐4‐methoxyquinolines in moderate to high yield [69].…”

Section: Application Of Cross‐coupling Reactions In the Synthesis Of mentioning

confidence: 99%

Halogenated Quinolines as Substrates for the Palladium‐Catalyzed Cross‐Coupling Reactions to Afford Substituted Quinolines

Mphahlele

Lesenyeho

2013

Journal of Heterocyclic Chem

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View this article online at wileyonlinelibrary.com.The use of palladium complexes in catalyzing the cross-coupling of halogenated quinolines with various organometalic reagents has led to the development of radically new methods of synthesizing novel substituted quinoline derivatives. The focus of this review is on the application of the following palladium-catalyzed reactions of halogenated quinolines with organometalic reagents to afford substituted quinoline derivatives: Kumada, Stille, Negishi, Sonogashira, Suzuki, Heck, and Hiyama cross-coupling reactions. Scheme 4. Palladium-catalyzed coupling of the 4-bromoquinoline derivatives with zinc cyanide. Reagents and conditions: (i) Zn(CN) 2 , Pd(PPh 3 ) 4 , DMF, 80°C; (ii) Pyr·HBr, 200°C. Scheme 3. Palladium-catalyzed Negishi cross-coupling of quinolyl zinc iodides with organoiodides. Reagents and conditions: (i) Zn, DMA; (ii) Pd(dba) 2 , P(o-furyl) 3 , THF, room temperature or heat (for 13c, e, and f).4 M. Scheme 8. Successive Negishi cross-coupling of 2,6-dibromoquinoline with organozinc reagents. Reagents and conditions: (i) Pd(OAc) 2 , P(o-furyl) 3 , PhMe/DMA; (ii) [ 14 C]-MeZnI; NiCl 2 (dppp); THF. Scheme 9. Palladium-phosphinous acid-catalyzed alkynylation of 4-chloroquinoline. Reagents and conditions: (i) POPd, TBAB, NaOH, CuI, H 2 O, 5 h. Scheme 10. One-pot palladium/CuI-catalyzed dialkynylation of 2,4-dichloroquinoline. Reagents and conditions: (i) Pd/C, PPh 3 , CuI, NEt 3 , water, 80-85°C. 6 M.

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One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids

Cited by 11 publications

References 31 publications

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2,4-Diarylquinolines: Synthesis, Absorption and Emission Properties

Halogenated Quinolines as Substrates for the Palladium‐Catalyzed Cross‐Coupling Reactions to Afford Substituted Quinolines

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