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

Xiaoyuan Wan,

Huawen Huang,

Deng Yujie

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7707 - 7712

Published: Aug. 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

Language: Английский

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

Xiaoting Gu,

Maoyi Dai,

Xirui Qing

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10272 - 10282

Published: July 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.

Language: Английский

Citations

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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3583 - 3588

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6694 - 6699

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 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.

Language: Английский

Citations

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

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(93), P. 13835 - 13838

Published: Jan. 1, 2023

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

Language: Английский

Citations

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

Yuito Kobori,

Shota Asai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(36), P. 7343 - 7348

Published: Jan. 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.

Language: Английский

Citations

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

Xiaoyuan Wan,

Huawen Huang,

Deng Yujie

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7707 - 7712

Published: Aug. 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

Language: Английский

Citations

0