Directing-group-free strategy for the iodine-mediated regioselective dichalcogenation of indolines: understanding the full catalytic cycles DOI
Xiaoxiang Zhang, Chenrui Liu,

Wenwei Pang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 871 - 884

Published: Dec. 11, 2023

A metal-free catalytic method for the regioselective direct dehydrogenation–dichalcogenation of indolines. The reaction mechanism and regioselectivity have been elucidated via density functional theory studies.

Language: Английский

Iodine-dependent oxidative regioselective aminochalcogenation of indolines DOI
Xiaoxiang Zhang, Chenrui Liu, Wanxing Wei

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(9), P. 1152 - 1155

Published: Jan. 1, 2024

An efficient approach for the selective construction of C2,3- or C2,5-aminochalcogenated indole derivatives has been developed, which enables oxidative regioselective aminochalcogenation indolines with amines and dichalconides.

Language: Английский

Citations

7
Iodine-Mediated C2,3–H Aminoheteroarylation of Indoles DOI

Maoyi Dai,

Yingying Zhang, Xiaoxiang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15106 - 15117

Published: Oct. 21, 2023

A metal-free one-pot oxidative cross-dehydrogenation coupling reaction for the formation of C-N/C-C bonds at C2,3-positions indoles with azoles and quinoxalinones has been developed. The proposed method several notable features, including catalysis, use N-H free as substrates, ease operation, mild conditions, compatibility a wide range substrates.

Language: Английский

Citations

9
One-pot Multicomponent Tandem Reaction for the Rapid Synthesis of 2-Amino-3-benzylindoles DOI
Pengyan Zhang, Chenrui Liu,

Maoyi Dai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel one-pot oxidative cross-dehydrogenation coupling (CDC) reaction has been developed for the selective construction of C–N and C–C bonds at C2,3-positions indoles.

Language: Английский

Citations

0
Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines DOI
Xiaoxiang Zhang, Xiaoting Gu, Yingying Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1933 - 1940

Published: Jan. 1, 2024

A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via successive regioselective chalcogenation, oxidation, amination and halogenation.

Language: Английский

Citations

3
Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles DOI
Yingying Zhang, Xiaoxiang Zhang,

Junqiu Liao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7216 - 7224

Published: May 2, 2024

An organoselenium-catalyzed C2,3-diarylation of unprotected N–H indoles with electron-rich aromatics has been developed. This one-pot multicomponent tandem cross-dehydrogenation coupling reaction allows for the incorporation two different aromatic groups to indoles. More importantly, this approach offers significant advantages, including a high atom and step economy, eliminating need prepreparation substrates, streamlining synthetic process enhancing its practicality. Overall, presents an efficient versatile strategy functionalization indole derivatives.

Language: Английский

Citations

3
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

3
Organo-catalyzed C2,3–H aminochalcogenation of indoles with secondary (aliphatic) amines DOI
Xiaoxiang Zhang, Chenrui Liu, Yingying Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5886 - 5894

Published: Jan. 1, 2023

A direct C2,3–H difunctionalization of indoles with unactivated amines facilitated by the organo-chalconium catalyst generated through reaction iodine and chalconium reagents has been developed.

Language: Английский

Citations

7
Directing-group-free strategy for the iodine-mediated regioselective dichalcogenation of indolines: understanding the full catalytic cycles DOI
Xiaoxiang Zhang, Chenrui Liu,

Wenwei Pang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 871 - 884

Published: Dec. 11, 2023

A metal-free catalytic method for the regioselective direct dehydrogenation–dichalcogenation of indolines. The reaction mechanism and regioselectivity have been elucidated via density functional theory studies.

Language: Английский

Citations

4