Indium(III) Trifluoromethanesulfonate: An Efficient Reusable Catalyst for the Alkynylation-Cyclization of 2-Aminoaryl Ketones and Synthesis of 2,4-Disubstituted Quinolines

Lekhok, Kushal C.; Prajapati, Dipak; Boruah, Romesh C.

doi:10.1055/s-2008-1042800

Cited by 10 publications

(3 citation statements)

References 6 publications

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“…This reaction takes place in ionic liquid medium ([hmim]PF 6 ) in the presence of zinc trifluoromethanesulfonate catalyst [3]. Lekhok et al synthesized the same product in the presence of catalytic amount of indium(III) trifluoromethanesulfonate (In(CF 3 SO 3 ) 3 ) under microwave and solvent-free conditions [4]. Quinoline Heterocycles: Synthesis and Bioactivity DOI: http://dx.doi.org/10.5772/intechopen.81239 2,4-Diphenyl-2-methyl-1,2-dihydroquinoline, 4 has been prepared by the condensation followed by cyclization of aniline and acetophenone.…”

Section: Synthesismentioning

confidence: 99%

Quinoline Heterocycles: Synthesis and Bioactivity

Rajesh¹

2020

Heterocycles - Synthesis and Biological Activities

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Among heterocyclic compounds, quinoline is a privileged scaffold that appears as an important construction motif for the development of new drugs. Quinoline nucleus is endowed with a variety of therapeutic activities, and new quinolone derivatives are known to be biologically active compounds possessing several pharmacological activities. Many new therapeutic agents have been developed by using quinoline nucleus. Hence, quinoline and its derivatives form an important class of heterocyclic compounds for the new drug development. Numerous synthetic routes have been developed for the synthesis of quinoline and its derivatives due to its wide range of biological and pharmacological activities. The article covers the synthesis as well as biological activities of quinoline derivatives such as antimalarial, anticancer, antibacterial, anthelmintic, antiviral, antifungal, antiinflammatory, analgesic, cardiovascular, central nervous system, hypoglycemic, and miscellaneous activities.

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Section: Synthesismentioning

confidence: 99%

Quinoline Heterocycles: Synthesis and Bioactivity

Rajesh¹

2020

Heterocycles - Synthesis and Biological Activities

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“…A 2005 study by Nakamura and co-workers provides a good example of Kumada coupling of aryl fluorides with aryl Grignard reagents . Prajapati and co-workers showed in 2008 an indium(II)-catalyzed Sonogashira-type cross-coupling between phenylacetylene and phenyl fluoride . Both Suzuki–Miyaura and Stille couplings of aryl fluorides (especially activated substrates) can be effectively achieved with a Pd catalyst. , In 2007, Love and co-workers demonstrated a Pt-catalyzed Negishi-type directed coupling of (poly)fluoroaryl imines with dimethylzinc …”

Section: Introductionmentioning

confidence: 99%

Fe-Promoted C–F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

Radzhabov

Mankad

2023

Organometallics

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Metal-mediated aryl fluoride activation not only presents challenges because of the thermodynamically robust C–F bond but also provides opportunities to develop C–C coupling reactions with this unconventional electrophile. Here, we report that the metallanucleophile, K[CpFe(CO)2] (KFp), is readily arylated by aryl fluorides to provide CpFe(CO)2Ar (FpAr) complexes under ambient conditions in the absence of any catalyst, contrary to previous literature reports. This C–F activation likely proceeds by a SNAr mechanism rather than the more common oxidative addition pathway for metal-mediated C–F cleavage. Facile access to FpAr derivatives has enabled further development of Fe-promoted coupling reactions of aryl fluorides with alkenes and alkynes. Under stoichiometric Fe conditions, Heck-type coupling reactions with aryl fluoride electrophiles are reported herein. Various aryl fluorides were found to couple with olefins to provide E-alkene products; aliphatic derivatives unexpectedly underwent reduction to 1,2-disubstituted ethane products to varying extents. Aryl fluorides were also found to couple with 5-decyne to yield indene derivatives in a one-pot manner; indenone and indanone products were also observed in selected cases. A mechanistic investigation to identify the apparently potent hydride donor generated under these conditions was conducted, leading to a mechanistic hypothesis involving the intermediacy of metal carbonyl-capped, triple-decker ferrocene compounds as reductants. Despite the involvement of these di-iron intermediates limiting stoichiometric product yields, the observed C–C coupling reactions expand the limits of organofluorine chemistry.

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“…showed in 2008 an indium(II)-catalyzed Sonogashira-type cross-coupling between phenylacetylene and phenyl benzene. 30 Both Suzuki-Miyaura and Stille couplings of aryl fluorides (especially activated substrates) can be effectively achieved with a Pd catalyst. 27,31 In 2007 Love et al demonstrated a Pt-catalyzed Negishi-type directed coupling of (poly)fluoroaryl imines with dimethylzinc.…”

Section: Introductionmentioning

confidence: 99%

Fe-Promoted C-F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

Radzhabov

Mankad

2023

Preprint

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Metal-mediated aryl fluoride activation presents challenges because of the thermodynamically robust C-F bond but also provides opportunities to develop C-C coupling reactions with this unconventional electrophile. Here, we report that the metallanucleophile, K[CpFe(CO)2] (KFp), is readily arylated by aryl fluorides to provide CpFe(CO)2Ar (FpAr) complexes at ambient conditions in the absence of any catalyst, contrary to previous literature reports. This C-F activation likely proceeds by a SNAr mechanism rather than the more common oxidative addition pathway for metal-mediated C-F cleavage. Facile access to FpAr derivatives has enabled further development of Fe-promoted coupling reactions of aryl fluorides with alkenes and alkynes. Under stoichiometric Fe conditions, the first documented examples of Heck-type coupling reactions with aryl fluoride electrophiles are reported herein. Various aryl fluorides were found to couple with olefins to provide E-alkene products; aliphatic derivatives unexpectedly underwent reduction to 1,2-disubsituted ethane products to varying extents. Aryl fluorides were also found to couple with 5-decyne to yield indene derivatives in a one-pot manner; indeneone and indanone products were also observed in selected cases. A mechanistic investigation to identify the apparently potent hydride donor generated under these conditions was conducted, leading to a mechanistic hypothesis involving the intermediacy of metal carbonyl-capped, triple-decker ferrocene compounds as reductants. Despite the involvement of these diiron intermediates limiting stoichiometric product yields, the observed C-C coupling reactions expand the limits of organofluorine chemistry.

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Indium(III) Trifluoromethanesulfonate: An Efficient Reusable Catalyst for the Alkynylation-Cyclization of 2-Aminoaryl Ketones and Synthesis of 2,4-Disubstituted Quinolines

Cited by 10 publications

References 6 publications

Quinoline Heterocycles: Synthesis and Bioactivity

Quinoline Heterocycles: Synthesis and Bioactivity

Fe-Promoted C–F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

Fe-Promoted C-F Activation of Aryl Fluorides Enables Heck-Type Coupling with Alkenes and One-Pot Synthesis of Indenes

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