Palladium‐Catalyzed C3‐Carbaldehyde Directed Regioselective C2‐Thioarylation of Indoles DOI

Sandip Kumar Gupta,

Niranjan Panda

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(11)

Published: April 5, 2024

Palladium-catalyzed thioarylation of indoles by diaryl disulfides in the presence phenyliododiacetate is reported. The directing potential weakly coordinating aldehyde group present at 3-position indole was exploited for regioselective C2-H over possible C4-H functionalization. Mechanistic studies reveal that process involves initial generation thioaryl radical followed sequential C-H activation, thiolate transfer, and reductive elimination.

Language: Английский

Tryptophan-specific modification and diversification of peptides and proteins DOI
S K Kundu, A. Bandyopadhyay, Rajib Sarkar

et al.

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

Published: Jan. 1, 2025

This review provides an account of the tryptophan-specific conjugation peptides and proteins its extensive application in imaging living cells, radiolabelling proteins, protein engineering, etc .

Language: Английский

Citations

3
Post-synthetic Chemical Functionalization of Peptides DOI

Stephanie A. Barros,

Rosaura Padilla‐Salinas, Irini Abdiaj

et al.

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Pd-Catalyzed Picolinamide-Directed C(sp2)–H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates DOI

Raghunath Bag,

Nagendra K. Sharma

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10127 - 10147

Published: June 26, 2024

This report describes a Pd-catalyzed picolinamide-directed site-selective C(sp

Language: Английский

Citations

2
Ag(I)-Mediated Site-Selective C(sp2)-H Chalcogenation of Tryptophan-Peptides with Dichalcogenides at Room Temperature DOI

Raghunath Bag,

Malobika Kar, Nagendra K. Sharma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 14981 - 15002

Published: Oct. 7, 2024

This report presents a silver-mediated site-selective chalcogenation of tryptophan-containing peptides with various dichalcogenides (disulfides/diselenides) at room temperature in good to excellent yields. The significant features include broad substrate scope, functional group diversity, late-stage modification drug molecules (Dopamine and Levodopa), valuable postsynthetic transformations under mild conditions.

Language: Английский

Citations

1
Pd-Catalyzed Picolinamide-Directed C(sp2)-H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates DOI Creative Commons
Nagendra K. Sharma,

Raghunath Bag

Published: March 5, 2024

This report describes a Pd-catalyzed picolinamide-directed site-selective C(sp2)-H sulfonylation of amino acids and peptides with sodium sulfinate in moderate to good yields. Sulfonylation levodopa dopamine drug molecules late-stage di-rected peptide are studied for the first time. Broad substrate scope having various functionalities, modifications, post synthetic utilities such as chalcogenation, bromination, olefination, arylation potential ad-vantages.

Language: Английский

Citations

0
Palladium‐Catalyzed C3‐Carbaldehyde Directed Regioselective C2‐Thioarylation of Indoles DOI

Sandip Kumar Gupta,

Niranjan Panda

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(11)

Published: April 5, 2024

Palladium-catalyzed thioarylation of indoles by diaryl disulfides in the presence phenyliododiacetate is reported. The directing potential weakly coordinating aldehyde group present at 3-position indole was exploited for regioselective C2-H over possible C4-H functionalization. Mechanistic studies reveal that process involves initial generation thioaryl radical followed sequential C-H activation, thiolate transfer, and reductive elimination.

Language: Английский

Citations

0