Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion DOI Open Access
Haoyang Liu,

Shuang-Shuang Sun,

Xian‐Li Ma

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(9), С. 2867 - 2867

Опубликована: Янв. 1, 2022

Язык: Английский

Visible-Light-Promoted Radical Cascade Sulfone Alkylation/Cyclization of 2-Isocyanoaryl Thioethers Enabled by Electron Donor–Acceptor Complex Formation DOI

Jiamei Shen,

Hui Li, Li Yuan

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10223 - 10233

Опубликована: Июнь 28, 2024

A photo-induced cascade sulfone alkylation/cyclization of 2-isocyanoaryl thioethers is explored. This visible-light-triggered reaction not only occurs under extremely mild conditions but also does require the presence a photosensitizer. The photocatalytic process triggered by photochemical activity in situ-generated electron donor–acceptor complexes, arising from association and α-iodosulfones. radical pathway was confirmed UV–vis spectroscopy, trapping, Job's plot, on/off irradiation experiments.

Язык: Английский

Процитировано

2

Visible-light-induced tandem difluoroalkylated spirocyclization of N-arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones DOI
Jinwei Yuan,

Lu Shen,

Mengyao Ma

и другие.

New Journal of Chemistry, Год журнала: 2022, Номер 46(9), С. 4470 - 4482

Опубликована: Янв. 1, 2022

A visible-light-catalyzed difluoroacetylated spirocyclization of N -arylpropiolamides with ethyl bromodifluoroacetate as a CF 2 CO Et radical precursor is described using fac -[Ir(ppy) 3 ] photocatalyst.

Язык: Английский

Процитировано

9

Recent Advances in Photocatalytic Reactions with Isocyanides DOI Open Access
Yan He,

Tianzi Huang,

Xiaoqin Shi

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(12), С. 4220 - 4220

Опубликована: Янв. 1, 2022

Isocyanides are a class of valuable C1 building blocks, widely used in organic chemistry, combinatorial biomedicine and other fields, their derivatives effective blocks for the synthesis bioactive molecules complex natural products.Herein, recent advances photocatalytic reactions with isocyanides summarized according to types reaction mechanism.The photocatalyst, substrate range mechanism emphatically discussed.Finally, challenges future development trends this research field discussed prospected.Keywords isocyanide; visible

Язык: Английский

Процитировано

7

A Facile Synthesis of Indole Derivatives by a Palladium‐Catalyzed Process Initiated from Ugi Adducts and their Antifungal Activities DOI

Ji‐Ying Qiu,

Ding Yuan, Jingjing Yu

и другие.

ChemistrySelect, Год журнала: 2021, Номер 6(45), С. 12921 - 12925

Опубликована: Дек. 2, 2021

Abstract In this work, an efficient synthesis of indole derivatives through palladium‐catalyzed double isocyanide insertion reactions has been developed. The reaction intermediates could be readily obtained by Ugi reactions. transformation features broad functional‐group compatibility, commercially available starting materials, and moderate to good yields. Furthermore, the bioactivities synthesized compounds were evaluated in mycelial growth tests against Penicilium digitatum Colletotrichun gloeosporioides, showed potential antifungal activities.

Язык: Английский

Процитировано

9

Shining light on tryptamine-derived isocyanides: access to constrained spirocylic scaffolds DOI Creative Commons
Minghui Wu, Jordy M. Saya, Peiliang Han

и другие.

Chemical Science, Год журнала: 2024, Номер 15(18), С. 6867 - 6873

Опубликована: Янв. 1, 2024

Tryptamine-derived isocyanides form aggregates at higher concentration that can a charge transfer complex under visible light irradiation thus enabling crucial single electron step to generate carbon-based-radical intermediates.

Язык: Английский

Процитировано

1

Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines DOI Creative Commons
Suven Das

ACS Omega, Год журнала: 2024, Номер unknown

Опубликована: Авг. 13, 2024

Dearomatization approaches are attractive for their abilities to transform simple, planar arenes into complex, three-dimensional architectures. In particular, visible-light driven dearomatization strategies significant because of mild, green, and sustainable nature, enabling the fabrication new chemical bonds via an electron transfer or energy process. Indole compounds, being potentially bioactive readily accessible, can be employed efficiently as building blocks constructing diverse annulated frameworks under photocatalysis. Highly stereoselective radical cascade reactions appropriate indole systems provide complex cyclic scaffolds bearing multiple stereocenters. fact, past few years have witnessed renaissance dearomative cycloadditions indoles visible-light-induced The present review highlights recent advances (2019–mid 2024) in visible-light-driven annulation leading formation polycyclic indolines, including angularly fused spiro indolines. Most described this providing quick access desired products. Additionally, characteristic reaction mechanisms offered understand how show distinctive reactivity photocatalytic conditions.

Язык: Английский

Процитировано

1

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis DOI Creative Commons
Akiya Ogawa, Yuki Yamamoto

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2114 - 2128

Опубликована: Авг. 26, 2024

Isocyanide is a promising synthetic reagent not only as one-carbon homologation but also nitrogen source for nitrogen-containing molecules. Because of their isoelectronic structure with carbon monoxide, isocyanides react nucleophiles, electrophiles, radicals, and transition metal reagents, are widely used in organic synthesis. On the other hand, use reactions heteroatom radicals limited. However, reaction tool construction molecules modified variety heteroatoms. In this Perspective, we review addition cyclization discuss prospects radicals.

Язык: Английский

Процитировано

1

Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones DOI

Kaixia Sui,

Yuting Leng, Panpan Wang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(51), С. 11184 - 11189

Опубликована: Дек. 12, 2024

A visible-light-induced radical cyclization of α-brominated amides has been developed to construct benzimidazole[2,1-

Язык: Английский

Процитировано

1

A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides DOI Creative Commons
Tarannum Tasnim, Negin Shafiei,

Katelyn J. Laminack

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 19, 2024

While charge-transfer complexes involving halogen-bonding interactions have emerged as an alternative strategy for the photogeneration of carbon radicals, examples using (fluoro)alkyl bromides are limited. This report describes a dual catalytic approach radical generation from α-bromodifluoroesters and amides under visible-light irradiation. Mechanistic studies suggest that reaction proceeds through in situ bromide displacement iodide salt, generating C–I bond can be engaged by our photocatalysis platform.

Язык: Английский

Процитировано

1

Synthesis of Azepinoindoles via Pd-Catalyzed C(sp2)–H Imidoylative Cyclization Reactions DOI
Jiang Wang,

Pinzhuo Ren,

Gongping Gu

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(15), С. 9663 - 9674

Опубликована: Июнь 13, 2022

An efficient and convenient method for the construction of diverse free (N-H)-benzazepinoindoles by Pd-catalyzed C(sp2)-H imidoylative cyclization 3-(2-isocyanobenzyl)-1H-indoles was developed. The reaction shows a wide substrate scope can be scaled up, providing practical route to valuable bioactive azepinoindoles.

Язык: Английский

Процитировано

6