5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp3)−H Addition and Removal by Base‐Triggered Cyclization DOI
Jizhou Song, Takeru Torigoe, Yoichiro Kuninobu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(46)

Published: Oct. 10, 2023

Abstract The 5‐ammonium‐4,4‐dimethylvaleryl (Amv) group was generated by conversion of acryloyl through decatungstate‐catalyzed addition C(sp 3 )−H bond i ‐BuNH 2 ⋅HCl under the irradiation UV light (365 nm or 405 nm). Treatment Amv‐protected alcohols and anilines with aqueous Na CO promoted efficient deprotection Amv. This is a unique method for removal groups from phenols, alcohols, anilines. selective Amv in presence another acetyl benzoyl demonstrated. base‐triggered intramolecular cyclization monitored release fluorescent molecule, it found that very rapid (within 1 min) some weak bases such as 2,6‐lutidine are sufficient to promote cyclization.

Language: Английский

Magnetically recoverable catalysts for efficient multicomponent synthesis of organosulfur compounds DOI Creative Commons
Fadhil Faez Sead, Vicky Jain, Anjan Kumar

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(5), P. 3928 - 3953

Published: Jan. 1, 2025

This review studies magnetically recoverable catalysts designed for the efficient multicomponent synthesis of organosulfur compounds. These enhance process by combining efficiency with environmental sustainability.

Language: Английский

Citations

7

Tetrabutylammonium decatungstate (TBADT), a compelling and trailblazing catalyst for visible-light-induced organic photocatalysis DOI
Bor‐Cherng Hong, Ranadheer Reddy Indurmuddam

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(19), P. 3799 - 3842

Published: Jan. 1, 2024

Tetrabutylammonium decatungstate (TBADT) has recently emerged as an intriguing photocatalyst under visible-light or near-visible-light irradiation in a wide range of organic reactions that were previously not conceivable. Given its ability to absorb visible light and excellent effectiveness activating unactivated chemical bonds, it is promising addition traditional photocatalysts. This review covers some the contemporary developments photocatalysis enabled by TBADT catalyst 2023, with contents organized reaction type.

Language: Английский

Citations

14

TBADT‐Mediated Photocatalytic Stereoselective Radical Alkylation of Chiral N‐Sulfinyl Imines: Towards Efficient Synthesis of Diverse Chiral Amines DOI Creative Commons
Matteo Leone, Joseph P. Milton, Dorota Gryko

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(24)

Published: Feb. 20, 2024

Abstract Herein we describe a sustainable and efficient photocatalytic method for the stereoselective radical alkylation of chiral sulfinyl imines. By employing readily available non‐prefunctionalized precursors cost‐effective TBADT as direct HAT photocatalyst, successfully obtain diverse amines with high yields excellent diastereoselectivity under mild conditions. This provides an approach accessing array medicinally relevant compounds, including both natural synthetic α‐amino acids, aryl ethyl amines, other structural motifs commonly found in approved pharmaceuticals product.

Language: Английский

Citations

12

Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles DOI Creative Commons

Emeric Montinho‐Inacio,

Damien Bouchet, Wei‐Yang Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)

Published: April 16, 2024

Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.

Language: Английский

Citations

8

Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer DOI
Dan Yang,

Yu-Tong Mei,

Ziyi Guo

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

Carboxylic acids are bench-stable and readily available chemical feedstocks that function as optimal fundamental synthetic platforms for the construction of C(sp3)–C(sp3) bonds via decarboxylation processes. We present a novel practical protocol decarboxylative alkylation Morita–Baylis–Hillman acetates with various carboxylic photoinduced iron-mediated ligand-to-metal charge transfer (LMCT) process under redox-neutral conditions. This method exhibits remarkable tolerance to wide array acids, including primary, secondary, tertiary obviating requirement preactivated radical precursors. The preliminary mechanistic analyses indicate pathway is involved in this catalytic transformation.

Language: Английский

Citations

0

Visible light-mediated decarboxylative allylic alkylation of Morita–Baylis–Hillman acetates with unactivated aliphatic acids DOI
Hui Zhang, Dan Yang,

Yu-Tong Mei

et al.

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

Published: Jan. 1, 2025

Herein, a visible light-induced and metal-free strategy for the direct decarboxylative allylic alkylation of Morita–Baylis–Hillman acetates with aliphatic acids under redox-neutral conditions has been developed.

Language: Английский

Citations

0

Modular access to diarylmethyl sulfonamides via visible light-promoted cross-coupling reactions DOI

Yu-Tong Mei,

Hui Zhang, Yu Jiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(65), P. 8589 - 8592

Published: Jan. 1, 2024

A novel and efficient method for the preparation of diarylmethyl sulfonamide derivatives has been achieved by visible-light-induced sulfamoylation para -quinone methides with sulfamoyl chlorides under mild metal-free conditions.

Language: Английский

Citations

2

Synthesis and Functionalization of Natural Products with Light-Driven Reactions DOI
Suman Majee, Km. Anjali, Satya P. Yadav

et al.

Published: Dec. 31, 2024

Language: Английский

Citations

1

Synthesis of sulfonated naphthols via metal-free oxidative coupling of beta-tetralone and sodium sulfinates DOI

Saiwen Liu,

H. Xiao, Jin Zhang

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 148, P. 155209 - 155209

Published: Aug. 3, 2024

Language: Английский

Citations

0

5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp3)−H Addition and Removal by Base‐Triggered Cyclization DOI
Jizhou Song, Takeru Torigoe, Yoichiro Kuninobu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(46)

Published: Oct. 10, 2023

Abstract The 5‐ammonium‐4,4‐dimethylvaleryl (Amv) group was generated by conversion of acryloyl through decatungstate‐catalyzed addition C(sp 3 )−H bond i ‐BuNH 2 ⋅HCl under the irradiation UV light (365 nm or 405 nm). Treatment Amv‐protected alcohols and anilines with aqueous Na CO promoted efficient deprotection Amv. This is a unique method for removal groups from phenols, alcohols, anilines. selective Amv in presence another acetyl benzoyl demonstrated. base‐triggered intramolecular cyclization monitored release fluorescent molecule, it found that very rapid (within 1 min) some weak bases such as 2,6‐lutidine are sufficient to promote cyclization.

Language: Английский

Citations

1