Copper(I)-Catalyzed Tandem Aminobenzannulation of Dienyne with Sulfonyl Azide

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3292 - 3303

Опубликована: Фев. 19, 2024

A general and efficient copper-catalyzed tandem aminobenzannulation of dienyne has been accomplished employing sulfonyl azides as a coupling partner. The reaction involves the formation both C–C C–N bonds via initial generation ketenimine from terminal alkyne azide followed by electrocyclic ring closure aromatization. developed is operationally simple allows synthesis diverse substituted aminonaphthalenes fused aminoarenes in good to excellent yields with high selectivities.

Язык: Английский

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Oxidative Remote Aryl Rearrangement of N-Cinnamyl-N-alkoxybenzyl Sulfonamides Using Hypervalent Iodine(III)

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8768 - 8773

Опубликована: Окт. 10, 2024

An oxidative remote aryl rearrangement of N-cinnamyl-N-alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization alkoxybenzene ring on benzyl group, which acts as good donor, inducing regioselective installation group and oxygen atom via cascade transformation. enantioselective using C2-symmetrical chiral iodoarene gave enantioenriched products enantioselectivity.

Язык: Английский

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Theoretical Study on the Copper-Catalyzed ortho-Selective C-H Functionalization of Naphthols with α-Phenyl-α-Diazoesters

Molecules, Год журнала: 2023, Номер 28(4), С. 1767 - 1767

Опубликована: Фев. 13, 2023

The aromatic C(sp2)-H functionalization of unprotected naphthols with α-phenyl-α-diazoesters under mild conditions catalyzed by CuCl and CuCl2 exhibits high efficiency unique ortho-selectivity. In this study, the combination density functional theory (DFT) calculations experiments is employed to investigate mechanism C-H functionalization, which reveals fundamental origin site-selectivity. It explains that CuCl-catalyzed ortho-selective functionlization due bimetallic carbene, differs from reaction via monometallic carbene. results demonstrate function favourable H-bond interactions on site- chemo-selectivity through stabilizing rate-determining transition states in proton (1,3)-migration.

Язык: Английский

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Group VIII metal difluorocarbene complexes: Synthesis and applications

Journal of Fluorine Chemistry, Год журнала: 2023, Номер 273, С. 110238 - 110238

Опубликована: Дек. 27, 2023

Язык: Английский

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Rhodium(ii)-catalyzed synthesis of 2-aminoquinoline derivatives from 2-quinolones and N-sulfonyl-1,2,3-triazoles

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(41), С. 8267 - 8272

Опубликована: Янв. 1, 2023

Herein, we disclose a rhodium(II) catalyzed efficient and convenient method for the synthesis of 2-aminoquinoline derivatives from 2-quinolones N-sulfonyl-1,2,3-triazoles. The reaction provides rapid access to series 2-aminoquinolines with moderate excellent yields. proceeds via quinolone-hydroxyquinoline tautomerization/O-H insertion rhodium(II)-aza vinyl carbene intermediate generated by denitrogenation triazole followed rearrangement deliver desired product. Furthermore, demonstrated iodine-mediated dealkylation derivative.

Язык: Английский

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α-Carbonyl Rh-Carbenoid Initiated Cascade Assembly of Diazobarbiturates with Alkylidene Pyrazolones for Synthesis of Spirofuropyrimidines

Molecules, Год журнала: 2024, Номер 29(13), С. 3178 - 3178

Опубликована: Июль 3, 2024

Catalyzed by Rh2(esp)2 (10 mol%) and (±)-BINAP (20 in DCE at 80 °C, the cascade assembly between diazobarbiturates alkylidene pyrazolones proceeded readily produced spiro-furopyrimidines 38–96% chemical yields. The structure of prepared spirofuro-pyrimidines was firmly confirmed X-ray diffraction analysis.

Язык: Английский

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