Anti-Markovnikov Hydroacylation of Aryl Alkenes with Aldehydes Enabled by Photo/Cobalt Dual Catalysis DOI

Guanghao Ji,

Xuan Li, J. Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 28, 2024

Herein we describe a dual photo/cobalt-catalyzed anti-Markovnikov hydroacylation of aryl alkenes using aldehyde as acyl source. The key to success is the cobalt catalyzed hydrogen atom transfer, which enables effective formation desired products and efficient regeneration photocatalyst under mild conditions. This protocol features broad substrate scopes, good functional group tolerance, high efficiency regioselectivity.

Language: Английский

Recent advances of decatungstate photocatalyst in HAT process DOI
Praveen P. Singh, Surabhi Sinha, Prashant Gahtori

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2523 - 2538

Published: Jan. 1, 2024

The decatungstate anion (W

Language: Английский

Citations

29

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

15

Biomimetic Photoexcited Cobaloxime Catalysis in Organic Synthesis DOI Creative Commons
Phong Dam, Kaiming Zuo, Luis Miguel Azofra

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(33)

Published: May 22, 2024

Abstract Drawing inspiration from nature has long been a cornerstone of chemical innovation, with natural systems offering wealth untapped potential for discovery. In this minireview, we delve into the burgeoning field cobaloxime catalysis in organic synthesis, which mimics catalytic activity organometallic alkylcobalamine enzymes. Our focus lies on elucidating latest advancements area, as well delineating primary mechanistic pathways at play. By describing, and comparing these mechanisms, provide comprehensive overview current state‐of‐the‐art, while also shedding light key unresolved challenges that await further exploration.

Language: Английский

Citations

11

Cooperative Fe/Co-Catalyzed Remote Desaturation for the Synthesis of Unsaturated Amide Derivatives DOI
Yanjun Wan, Emmanuel Ramírez,

Ayzia Ford

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(7), P. 4985 - 4992

Published: Feb. 6, 2024

Unsaturated amides represent common functional groups found in natural products and bioactive molecules serve as versatile synthetic building blocks. Here, we report an iron(II)/cobalt(II) dual catalytic system for the syntheses of distally unsaturated amide derivatives. The transformation proceeds through iron nitrenoid-mediated 1,5-hydrogen atom transfer (1,5-HAT) mechanism. Subsequently, radical intermediate undergoes hydrogen abstraction from vicinal methylene by a cobaloxime catalyst, efficiently yielding β,γ- or γ,δ-unsaturated derivatives under mild conditions. efficiency Co-mediated HAT can be tuned varying different auxiliaries, highlighting generality this protocol. Remarkably, desaturation protocol is also amenable to practical scalability, enabling synthesis carbamates ureas, which readily converted into various valuable molecules.

Language: Английский

Citations

7

Synthesis of non-canonical amino acids through dehydrogenative tailoring DOI
Xin Gu,

Yu‐An Zhang,

Shuo Zhang

et al.

Nature, Journal Year: 2024, Volume and Issue: 634(8033), P. 352 - 358

Published: Aug. 29, 2024

Language: Английский

Citations

7

Strain-Inducing Positional Alkene Isomerization DOI
Vignesh Palani, Alison E. Wendlandt

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(36), P. 20053 - 20061

Published: Aug. 30, 2023

Small, strained ring systems are important pharmacophores in medicinal chemistry and versatile intermediates organic synthesis. However, the kinetic thermodynamic instability of many molecules renders them challenging to prepare. Here, we report a strain-inducing positional alkene isomerization reaction that provides mild selective access cyclobutene building blocks from readily obtained cyclobutylidene precursors. This endergonic relies on sequential synergistic action decatungstate polyanion photocatalyst cobaloxime co-catalyst store potential energy form strain. The versatility products is demonstrated through diverse subsequent strain-releasing transformations. Mechanistic studies reveal steric basis for strain-selective product formation.

Language: Английский

Citations

13

Unlock the C–N Bond Amidation of Enaminones: Metal-Free Synthesis of Enamides by Water-Assisted Transamidation DOI

Haozhi Wu,

Kang Chen, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 216 - 223

Published: Dec. 18, 2023

The C–N bond transamidation of primary amides with N,N-dimethyl enaminones has been efficiently realized by heating in the presence trifluoromethanesulfonic acid (TfOH). method enables practical synthesis valuable enamides without use any metal reagent. In addition, this protocol can also be expanded to reactions sulfonamides, and late-stage functionalization on sulfonamide drugs such as Celecoxib Valdecoxib verified. Moreover, participation water assisting process identified isotope labeling experiments using D2O, disclosing a new possibility designing catalytic tactic other reactions.

Language: Английский

Citations

13

Synthesis of Polysubstituted Enamides by Hydrogen Atom Transfer Alkene Isomerization Using Dual Cobalt/Photoredox Catalysis DOI

Yusuke Seino,

Yuto Yamaguchi,

Akihiko Suzuki

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(37)

Published: April 19, 2023

M-HAT isomerization is a highly reliable method to access thermodynamically stable alkenes with high functional group tolerance. However, synthesis of heteroatom-substituted by reaction still underdeveloped. Herein, we report an enamide using via combination cobalt and photoredox catalysis. This tolerates variety groups including haloarenes, heteroarenes, free hydroxy groups, non-protected indoles, drug derivatives. Furthermore, this can isomerize styrene derivatives in good yield E/Z selectivity.

Language: Английский

Citations

12

Photocatalytic water splitting versus H2 generation coupled with organic synthesis: A large critical review DOI
Aleksandr Savateev,

Jingru Zhuang,

Sijie Wan

et al.

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2025, Volume and Issue: 70, P. 44 - 114

Published: March 1, 2025

Language: Английский

Citations

0

Stereodivergent Construction of Enamides via a Radical-Mediated Isodesmic Reaction DOI
Yingying Xu, Xin Zhang, X. Kang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6749 - 6759

Published: April 10, 2025

Language: Английский

Citations

0