Nickel(II)‐Catalysed C–H Functionalization and Tandem Coupling of Terminal Alkynes with 1,3‐Dicarbonyls: Expedient Route to Functionalized Furans

Mohanty, Anuradha; Roy, Sujit

doi:10.1002/ejoc.201901309

Cited by 8 publications

(5 citation statements)

References 72 publications

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“…With regard to the synthetic challenge associated with C(sp 3 )−H/C(sp)−H coupling/cyclization sequence, Roy et al. in 2019 developed the synthesis of substituted furans 95 by dl ‐[Ni(Phen) 3 ]Cl 2 /Ag 2 CO 3 assisted coupling of alkynes 89 with 1,3‐dicarbonyl compounds 88 in good to excellent yields by C−H functionalization strategy [70] . Initially, activation of 1,3‐dicarbonyl by the L n Ni(II) catalyst 90 gives intermediate 91 .…”

Section: Transition‐metal Catalyzed Synthesismentioning

confidence: 99%

Synthesis of Polysubstituted Furans: An Update Since 2019

2023

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Polysubstituted furans are widespread structural motifs, extensively dispersed in natural products, in numerous bioactive compounds, pharmaceuticals, agrochemicals and organic functional materials. Hence, the development of rapid and competent methodologies for the synthesis of multisubstituted furans has drawn much attention over the years. This review summarizes the synthesis of polysubstituted furans using transition‐metal catalyzed, transition metal‐free, photochemical and electrochemical approaches with plausible mechanistic insights. In each reaction, the highest yields of di‐, tri‐ or tetrasubstituted furans are highlighted and some applications of the methodology towards the synthesis of natural products and biologically active compounds are mentioned. The present review highlights the recent progresses in the synthesis of polysubstituted furans reported from 2019 to 2023.

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Section: Transition‐metal Catalyzed Synthesismentioning

confidence: 99%

Synthesis of Polysubstituted Furans: An Update Since 2019

2023

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“…Benzyl 2- . 26 Purified by flash chromatography (eluent: PE/EA = 10:1) to afford a pale yellow oil (32.2 mg, 55%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.67 −7.62 (m, 2H), 7.48−7.43 (m, 2H), 7.43−7.40 (m, 2H), 7.40−7.37 (m, 2H), 7.37−7.33 (m, 1H), 7.30−7.26 (m, 1H), 6.92 (s, 1H), 5.32 (s, 2H), 2.67 (s, 3H).…”

Section: -(4-(tert-butyl)phenyl)-2-methylfuran-3-carboxylate (3c) 3fmentioning

confidence: 99%

Synthesis of Furans via Rhodium(III)-Catalyzed Cyclization of Acrylic Acids with α-Diazocarbonyl Compounds

Hong

Liu

et al. 2022

J. Org. Chem.

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An efficient protocol for the synthesis of furans through Rh(III)-catalyzed vinyl C–H activation from acrylic acids and α-diazocarbonyl compounds has been developed. The reaction features broad functional group tolerance and affords a series of furans in moderate to good yields. Moreover, no additives such as copper or silver salts are required. Some control experiments are performed to give insight into the mechanism of this cascade transformation and the decarbonylation process is involved in the formation of the furan product.

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“…Similarly, polycarbonylated compounds are valuable motifs. In particular, 1,3- and 1,4-dicarbonyl compounds are important building blocks in the synthesis of heterocycles . 1,4-Dicarbonyl compounds are mainly employed in the synthesis of pyrroles, furans, and thiophenes via the Paal–Knorr reaction (Scheme A–C).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones

Lima

Coelho

2020

ACS Omega

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We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita−Baylis− Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers in yields higher than 90%. The synthetic usefulness of this protocol was demonstrated by the conversion of selected ketones into biologically valuable α-alkylidene-γ-lactones upon reduction with sodium borohydride. In the course of the scope evaluation, we discovered that this methodology could also furnish α-arylidene-β,γbutenolides.

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Nickel(II)‐Catalysed C–H Functionalization and Tandem Coupling of Terminal Alkynes with 1,3‐Dicarbonyls: Expedient Route to Functionalized Furans

Cited by 8 publications

References 72 publications

Synthesis of Polysubstituted Furans: An Update Since 2019

Synthesis of Polysubstituted Furans: An Update Since 2019

Synthesis of Furans via Rhodium(III)-Catalyzed Cyclization of Acrylic Acids with α-Diazocarbonyl Compounds

Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones

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