Chemoselective Hydroheteroarylation of Alkenes via Photoredox-Neutral Proton- and BF3-Mediated Electron Transfer DOI

Xiaoyuan Wan,

Huawen Huang,

Deng Yujie

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7707 - 7712

Опубликована: Авг. 28, 2024

Herein, we have developed a complementary entry to enable hydroheteroarylation of alkenes involving basically photoredox dearomatizative heterocyclic carbon radical formation through acid-coupled electron transfer followed by Giese addition. While protonic solvent and thiophenol additive enabled two molecular hydroheteroarylations alkenes, the nonproton environment with BF

Язык: Английский

Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles DOI

Xiaoting Gu,

Maoyi Dai,

Xirui Qing

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10272 - 10282

Опубликована: Июль 5, 2024

The exploration of remote functionalization indoles is impeded by the inherently dominant reactivity intrinsic to pyrrole moiety. Herein, we delineate a novel strategy facilitated Lewis acid mediation, enabling C-H functionalization, which culminates in synthesis an array selectively functionalized indole derivatives, encompassing 3-trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride various acyl chlorides. Notably, protocol exhibits versatility, as epitomized extension C5-acylation alkylation sulfonation reactions. This methodology distinguished its exemplary regio- chemo-selectivity, extensive substrate scope, commendable tolerance diverse functional groups, employment comparatively mild reaction conditions.

Язык: Английский

Процитировано

2
Base-promoted fused β-carboline formation from 2-(1H-indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts DOI
Jinjin Chen, Yuxin Zhang, Xinping Liu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(13), С. 3583 - 3588

Опубликована: Янв. 1, 2024

A novel base-promoted fused β-carboline formation strategy from 2-(1 H -indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts has been developed. Ammonium served as nitrogen sources played an important role in selectivity control.

Язык: Английский

Процитировано

1
Access to tetrahydrocarbazoles via a photocatalyzed cascade decarboxylation/addition/cyclization reaction DOI
Shuai Han, Zhang Chen, Yu Guo

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(23), С. 6694 - 6699

Опубликована: Янв. 1, 2024

An efficient photocatalyzed decarboxylative coupling of indolepropionic acid NHPI esters with α,β-unsaturated carbonyl compounds has been developed, which provided structurally diverse tetrahydrocarbozles in moderate to good yields.

Язык: Английский

Процитировано

1
Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts DOI Open Access

Chang-Rui Nie,

Mei-Mei Pan,

Rong Deng

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Abstract We describe a selective preparation of variety functionalized pyrrolo[2,3‐ c ]tetrahydroquinolines and indolo[3,2‐ in 40–82% 40–80% yields from alkynyl‐tethered oximes with diaryliodonium triflates, respectively. The one‐pot reaction underwent N ‐arylation, intramolecular [3+2] cycloaddition, [1.3] or [3,3]‐rearrangement N−O bond total three steps. Experimental studies revealed that EtOAc solvent copper(II)‐catalyst played crucial roles on the formation these two tetrahydroquinoline scaffolds. Moreover, scaffolds could be converted into various building blocks by further transformations.

Язык: Английский

Процитировано

1
Regioselective synthesis of indazolo[2,3-a]quinazolines enabled by I2/S-facilitated annulation relay dehydrogenative aromatization of cyclohexanones DOI
Qinghe Gao,

Yimei Guo,

Penghui Cao

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(93), С. 13835 - 13838

Опубликована: Янв. 1, 2023

A method for concise and regioselective synthesis of indazolo[2,3- a ]quinazolines has been developed via sequential annulation dehydrogenative aromatization cyclohexanones.

Язык: Английский

Процитировано

3
Indoline hemiaminals: a platform for accessing anthranilic acid derivatives through oxidative deformylation DOI
Keisuke Tokushige,

Yuito Kobori,

Shota Asai

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(36), С. 7343 - 7348

Опубликована: Янв. 1, 2024

2-Aminobenzoyl chlorides possess both a nucleophilic nitrogen atom and an electrophilic carbonyl group, thus selective acylation of nucleophiles is challenging; self-dimerization sluggish reactions occur. Herein, we introduce new synthetic protocol using 2-aminobenzoyl surrogates, allowing concise entry to decorated derivatives in the absence transition metals, acid chlorides, specific reagents.

Язык: Английский

Процитировано

0
Chemoselective Hydroheteroarylation of Alkenes via Photoredox-Neutral Proton- and BF3-Mediated Electron Transfer DOI

Xiaoyuan Wan,

Huawen Huang,

Deng Yujie

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7707 - 7712

Опубликована: Авг. 28, 2024

Herein, we have developed a complementary entry to enable hydroheteroarylation of alkenes involving basically photoredox dearomatizative heterocyclic carbon radical formation through acid-coupled electron transfer followed by Giese addition. While protonic solvent and thiophenol additive enabled two molecular hydroheteroarylations alkenes, the nonproton environment with BF

Язык: Английский

Процитировано

0