A Lewis Acid‐Base Pair Catalyzed Dearomative Transformation of Unprotected Indoles via B−H Bond Activation DOI Open Access
Pinaki Nad, Arup Mukherjee

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(23)

Опубликована: Окт. 9, 2023

A sustainable and metal-free protocol has been described for the reduction of unprotected indoles. The catalytic system consists B(C6 F5 )3 THF as a Lewis acid-base pair that can activate B-H bond pincolborane (HBpin). encompasses broad substrate scope. Control experiments were conducted to understand possible intermediates involved during present protocol.

Язык: Английский

Palladium-Catalyzed Dearomative Heck/C(sp2)–H Activation/Decarboxylative Cyclization of C2-Tethered Indoles DOI
Shuyi Guo,

Wenbo Deng,

Xiaochang Xiao

и другие.

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9389 - 9394

Опубликована: Окт. 21, 2024

Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture the transient alkyl-Pd(II) species. Herein, we disclose a novel Heck/C(sp

Язык: Английский

Процитировано

3
Palladium-Catalyzed Domino Heck/Decarboxylative Cyanomethylation of Indoles and Alkenes with Cyanoacetate Salts DOI

Ping‐Xin Zhou,

Yang Liu, Mengjuan Li

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

A palladium-catalyzed reaction of indoles with cyanoacetate salts enables the synthesis 2,6-disubstituted indolines via tandem dearomatization/decarboxylative cyanomethylation. Remarkably, this is first example indole difunctionalization at C2 and C6 positions. Moreover, methodology extends to cyclization/decarboxylative cyanomethylation aryl halide-tethered alkenes.

Язык: Английский

Процитировано

0
Reusable Supported Pyridine-Mediated Cascade Synthesis of trans-2,3-Dihydroindoles via In Situ-Generated N-Ylide DOI
Anshul Jain,

Anitta Regina,

Akanksha Kumari

и другие.

Organic Letters, Год журнала: 2023, Номер 25(20), С. 3790 - 3795

Опубликована: Май 15, 2023

Merrifield resin-anchored pyridines were prepared and applied as reusable mediators for trans-selective cascade synthesis of 2,3-dihydroindoles. The developed approach relied on in situ N-ylide formation followed by Michael substitution reactions. reaction was also carried out efficiently with simple pyridine. products further transformed into synthetically valuable compounds, supported pyridine reused multiple cycles. Density functional theory calculations confirmed the trans-selectivity lower-energy pathway.

Язык: Английский

Процитировано

6
Enantioselective synthesis of 3a-azido-pyrroloindolines by copper-catalyzed asymmetric dearomative azidation of tryptamines DOI

Cheng-Zhou Lin,

Lingfeng Jiang, Guangyi Zhang

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(50), С. 7831 - 7834

Опубликована: Янв. 1, 2023

Copper-catalyzed asymmetric dearomative azidation of tryptamines using azidobenziodoxolone as an azidating reagent was developed, which affords a variety 3a-azido-pyrroloindolines in good to high enantioselectivities under mild reaction conditions. The azides could be readily transformed into the corresponding 3a-amino-pyrroloindolines via reduction and 1,2,3-triazole derivatives click reaction.

Язык: Английский

Процитировано

6
Synthesis of condensed tetra- and polycyclic nitrogen heterocycles with a five-membered azacyclic core induced by ionic palladium catalysts DOI
Árpàd Molnár

Coordination Chemistry Reviews, Год журнала: 2024, Номер 504, С. 215668 - 215668

Опубликована: Янв. 19, 2024

Язык: Английский

Процитировано

2
Synthesis of structurally diverse silicon-incorporated indolinesviasilyl radical-triggered radical cascade reactions DOI

Ye Tian,

Jinjin Zhao,

Wan-Xin Zheng

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(9), С. 2165 - 2170

Опубликована: Янв. 1, 2023

Structurally diverse silicon-incorporated indolines were synthesized via a silyl radical-triggered radical addition–translocation–cyclization (RATC) process.

Язык: Английский

Процитировано

5
Asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes by nickel catalysis DOI

Xinmiao Huang,

Xin Tan, Xu Zhang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(23), С. 5940 - 5949

Опубликована: Янв. 1, 2023

Herein, we report an asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes enabled by nickel catalysis to access structurally diverse gem -difluorovinyl-containing chiral polycyclic indolines.

Язык: Английский

Процитировано

4
Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4 + 1] annulation reactions of a sulfonium ylide DOI
Anshul Jain, Akanksha Kumari, Ramesh K. Metre

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(3), С. 621 - 632

Опубликована: Дек. 18, 2023

We have established an in situ generated sulfonium-ylide mediated annulation to construct 2,3-disubstituted-2,3-dihydroindoles and extended dihydrobenzofurans.

Язык: Английский

Процитировано

2
Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles DOI Creative Commons
Tingting Liu,

Jianbin Wang,

Rou Xiao

и другие.

RSC Advances, Год журнала: 2024, Номер 14(22), С. 15591 - 15596

Опубликована: Янв. 1, 2024

A strategy allowing the switchable divergent synthesis of chiral indole derivatives was established via phosphoric acid-catalyzed asymmetric dearomatization 2,3-disubstituted indoles using naphthoquinone monoimines as electrophiles. The products were switched between indolenines and fused indolines according to post-processing conditions. Both two types obtained in good high yields with generally excellent enantioselectivities. NaBH4 found work a promoter well reductant cyclization process leading indolines.

Язык: Английский

Процитировано

0
Visible Light-Induced Photocatalyst-Free Aromatic Amidation for the Synthesis of 3,4-Dihydroquinolin-2(1H)-ones DOI
Lingang Wu, Haibo Zhou, Lei Sun

и другие.

Russian Journal of Organic Chemistry, Год журнала: 2024, Номер 60(3), С. 459 - 466

Опубликована: Март 1, 2024

Язык: Английский

Процитировано

0