Synthesis of C2,3-vicinal diaminoindoles via a copper-iodine co-catalytic strategy DOI Open Access
Wenhua Yu, Yingying Zhang, Xiaoxiang Zhang

et al.

Authorea (Authorea), Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 16, 2023

A one-pot synthesis of vicinal diamines using indoles, pyrazoles, and phenothiazines in a tandem multi-component reaction is developed. The utilization copper-iodine co-catalytic system enables the generation diverse range diaminoindoles with good selectivity moderate to yields. An attractive aspect this method that it can be conducted under mild environmentally friendly conditions, showcasing its potential as an alternative approach for synthesizing diamines. Moreover, use multicomponent highlights power versatility such strategies synthetic chemistry.

Language: Английский

Strategies and Mechanisms of First-Row Transition Metal-Regulated Radical C–H Functionalization DOI
Xinghua Wang,

J. P. He,

Yanan Wang

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(17), P. 10192 - 10280

Published: Aug. 8, 2024

Radical C–H functionalization represents a useful means of streamlining synthetic routes by avoiding substrate preactivation and allowing access to target molecules in fewer steps. The first-row transition metals (Ti, V, Cr, Mn, Fe, Co, Ni, Cu) are Earth-abundant can be employed regulate radical functionalization. use such is desirable because the diverse interaction modes between metal complexes species including addition center, ligand complexes, substitution single-electron transfer radicals hydrogen atom noncovalent complexes. Such interactions could improve reactivity, diversity, selectivity transformations allow for more challenging reactions. This review examines achievements this promising area over past decade, with focus on state-of-the-art while also discussing existing limitations enormous potential high-value regulated these metals. aim provide reader detailed account strategies mechanisms associated

Language: Английский

Citations

16

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 oxidative triple functionalization of indolines with azoles and diazonium salts DOI
Yifeng Liu,

Xiaoting Gu,

Xiaoxiang Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(34), P. 4613 - 4616

Published: Jan. 1, 2024

We report an innovative synthetic strategy for the generation of polysubstituted indoles from indolines, aryldiazonium salts, and azoles. The methodology encompasses electrophilic substitution reaction affording C5-indoline intermediates which undergo iodine-mediated oxidative transformation coupled with C-H functionalization to yield indole derivatives.

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

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

Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks DOI
Weiwei Luo, Yu Zhang,

Meijun Ming

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6819 - 6849

Published: Jan. 1, 2024

This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications development this class five-membered heterocyclic frameworks.

Language: Английский

Citations

3

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

Synthesis of 2,3‐Diaminoindolesvia a Copper‐Iodine Co‐catalytic Strategy DOI
Wenhua Yu, Yingying Zhang, Xiaoxiang Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(24), P. 3567 - 3572

Published: Aug. 28, 2023

Comprehensive Summary A one‐pot synthesis of vicinal diamines using indoles, azoles and phenothiazines in a tandem multi‐component reaction is developed. The utilization copper‐iodine co‐catalytic system enables the generation diverse range diaminoindoles with good selectivity moderate to yields. An attractive aspect this method that it can be conducted under mild environmentally friendly conditions, showcasing its potential as an alternative approach for synthesizing diamines. Moreover, use multicomponent highlights power versatility such strategies synthetic chemistry.

Language: Английский

Citations

8