A Chemistry for Incorporation of Selenium into DNA‐Encoded Libraries DOI
Hongtao Xu,

Yuang Gu,

Shuning Zhang

et al.

Angewandte Chemie, Journal Year: 2020, Volume and Issue: 132(32), P. 13375 - 13382

Published: April 13, 2020

Abstract Conventional direct C−H selenylation suffers from simple selenation with limited atom economy and complicated reaction system. In this work, we designed benzoselenazolone as a novel bifunctional selenide reagent for both off‐ on‐DNA under rhodium(III) catalysis. We show that using allowed production of series products containing an adjacent aminoacyl group in fast efficient way, high economy. The synthetic application method was demonstrated by taking advantage the amide functionality nucleophile, directing group, coupling partner. This work shows great potential facilitating rapid construction selenium‐containing DNA‐encoded chemical libraries (SeDELs), lays foundation development drugs.

Language: Английский

Pd and photoredox dual catalysis assisted decarboxylative ortho-benzoylation of N-phenyl-7-azaindoles DOI

Shruti Rajput,

Ramandeep Kaur, Nidhi Jain

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(7), P. 1453 - 1461

Published: Jan. 1, 2022

The directing group assisted decarboxylative ortho-benzoylation of N-aryl-7-azaindoles with α-keto acids has been achieved by synergistic visible light promoted photoredox and palladium catalysis. approach tenders rapid entry to aryl ketone architectures from simple acid precursors via the in situ generation a benzoyl radical intermediate. transformation provides range ortho-benzoylated N-aryl-7-azaindoles, excellent site-selectivity good functional compatibility under mild reaction conditions. Biological target predictions indicate that these molecules may serve as potential anti-cancer anti-viral agents.

Language: Английский

Citations

12
Regioselective deoxygenative chalcogenation of 7-azindole N-oxides promoted by I2/PEG-200 DOI
Shanshan Liu, Heng Yang, Lin‐Yu Jiao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(47), P. 10073 - 10087

Published: Jan. 1, 2019

We developed a general and sustainable approach for the regioselective deoxygenative chalcogenation of 7-azindole N-oxides; combination internal oxidant green solvent has been used synthesis mono- dichalcogenyl azaindoles.

Language: Английский

Citations

18
Rhodium(iii)-catalyzed oxidative alkylation of N-aryl-7-azaindoles with cyclopropanols DOI
Jidan Liu,

Jinyuan Jiang,

Zhenke Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(5), P. 993 - 997

Published: Jan. 1, 2021

An efficient Rh(iii)-catalyzed C–H oxidative alkylation of N-aryl-7-azaindoles with cyclopropanols by merging tandem and C–C cleavage was developed.

Language: Английский

Citations

13
Cu(II)-Catalyzed C–N, C–O, C–Cl, C–S, and C–Se Bond Formation via C(sp2)–H Activation Using 7-Azaindole as an Intrinsic Directing Group DOI
Mohit Kumar,

Raziullah,

Gulraız Ahmad

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(21), P. 15185 - 15202

Published: Oct. 26, 2021

A general protocol has been developed for the construction of carbon-heteroatom (C-N, C-Cl, C-O, C-S, and C-Se) bonds using bench stable, earth-abundant, environmentally benign copper catalyst. Only oxygen is sufficient to regenerate Control experiments suggested that proto-demetalation step reversible. Depending on coupling partner, reaction follows either disproportionation or radical pathways complete catalytic cycle. The synthetic utility demonstrated via various functional group transformations.

Language: Английский

Citations

13
A Chemistry for Incorporation of Selenium into DNA‐Encoded Libraries DOI
Hongtao Xu,

Yuang Gu,

Shuning Zhang

et al.

Angewandte Chemie, Journal Year: 2020, Volume and Issue: 132(32), P. 13375 - 13382

Published: April 13, 2020

Abstract Conventional direct C−H selenylation suffers from simple selenation with limited atom economy and complicated reaction system. In this work, we designed benzoselenazolone as a novel bifunctional selenide reagent for both off‐ on‐DNA under rhodium(III) catalysis. We show that using allowed production of series products containing an adjacent aminoacyl group in fast efficient way, high economy. The synthetic application method was demonstrated by taking advantage the amide functionality nucleophile, directing group, coupling partner. This work shows great potential facilitating rapid construction selenium‐containing DNA‐encoded chemical libraries (SeDELs), lays foundation development drugs.

Language: Английский

Citations

14