Chemoselective Cleavage and Transamidation of Tertiary p-Methoxybenzyl Amides under Metal-Free Photoredox Catalysis DOI

Hee-Chan Jeong,

Hyo‐Jun Lee, Keiji Maruoka

et al.

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

Published: Oct. 21, 2024

A metal-free and mild cleavage of tertiary

Language: Английский

Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines DOI Creative Commons

Tian Hongjun,

Feng Jiang,

Xiaoming Wang

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(3)

Published: Jan. 17, 2025

Singly occupied molecular orbital (SOMO) activation of in situ generated enamines has achieved great success (asymmetric) α-functionalization carbonyl compounds. However, examples on the use this mode transformations other functional groups are rare, and combination SOMO with transition metal catalysis is still less explored. In area deoxygenative functionalization amides, intermediates such as iminium ions were often to result formation α-functionalized amines. contrast, direct deoxygenation amides β-functionalized amines highly appealing yet remains scarcely investigated. Here, a arylation aryl halides was developed via multicatalysis iridium/photoredox/nickel/iridium, affording β-aryl high efficiency. The key reaction enamine synergy Ni-catalyzed arylation, which conjunction two compatible Ir-catalyzed reduction processes.

Language: Английский

Citations

1
Electron-Donor-Mediated Divergent Transformation of Br–RF via EDA Complex for the Synthesis of Fluorine-Containing Oxindoles and Amides DOI
Shupeng Zhang,

Jin-Xin Lan,

Mei-Ling Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9990 - 9995

Published: Nov. 11, 2024

We have developed an unprecedented electron-donor-controlled divergent reaction between

Language: Английский

Citations

4
Synthesis of (–)-Sedacryptine and (–)-Geissman-Waiss Lactone by Applying Methods for the Direct Transformation of Amides DOI
Yanyan Xu,

Yi Ruan,

Jian‐Feng Zheng

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(3), P. 988 - 988

Published: Jan. 1, 2025

Language: Английский

Citations

0
Deoxygenative Alkynylation of Amides via C=O Bond Cleavage DOI
Lan Chen, Wei Zhou, Peixin Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(64), P. 8454 - 8457

Published: Jan. 1, 2024

A novel deoxygenative alkynylation of amides promoted by a synergistic action divalent rare-earth element and transition metal has been developed. In this method, α-alkynyl substituted amines are synthesized from unactivated alkynes in single transformation. Broad substrate scope excellent selectivity for CO cleavage demonstrated. This approach represents general method the construction versatile amide bonds.

Language: Английский

Citations

2
Recent Advances on Fluorine Chemistry DOI Open Access
Mikhail Yu. Moskalik

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(15), P. 8251 - 8251

Published: July 28, 2024

The purpose of this Special Issue is to showcase the latest findings in fluorine chemistry [...]

Language: Английский

Citations

1
Samarium Diiodide/Samarium-Mediated Direct Deoxygenative Hydroborylation of Ketones with Hydroborane Esters DOI
Yongqi Liang, Yilin Ma,

Wei Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A direct deoxygenative hydroborylation of ketones with hydroborane ester promoted by a combination samarium diiodide, and nickel has been developed.

Language: Английский

Citations

1
Deoxygenative Geminal Silylboration of Amides Using Silylboronates: Synthesis and Use of α‐Boryl‐α‐Silylalkylamines DOI

Koh Watanabe,

Kazunori Nagao, Hirohisa Ohmiya

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: Aug. 6, 2024

Abstract α‐Silylalkylamines and α‐borylalkylamines are versatile synthetic intermediates attractive scaffolds found in pharmaceutical drugs agrochemicals. Despite great progress on methods for preparation of α‐silylalkylamines or α‐borylalkylamines, there no general strategies α‐boryl‐α‐silylalkylamines the reactivity has not been explored. Here we report deoxygenative geminal silylboration amides using silylboronates presence alkoxide base catalyst, producing α‐boryl‐α‐silylalkylamines. The silicon boron groups to be utilized chemoselective transformations, such as protonation alkylation. This protocol serves various from readily available amides.

Language: Английский

Citations

0
Deoxygenative Geminal Silylboration of Amides Using Silylboronates: Synthesis and Use of α‐Boryl‐α‐Silylalkylamines DOI

Koh Watanabe,

Kazunori Nagao, Hirohisa Ohmiya

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: Aug. 6, 2024

Abstract α‐Silylalkylamines and α‐borylalkylamines are versatile synthetic intermediates attractive scaffolds found in pharmaceutical drugs agrochemicals. Despite great progress on methods for preparation of α‐silylalkylamines or α‐borylalkylamines, there no general strategies α‐boryl‐α‐silylalkylamines the reactivity has not been explored. Here we report deoxygenative geminal silylboration amides using silylboronates presence alkoxide base catalyst, producing α‐boryl‐α‐silylalkylamines. The silicon boron groups to be utilized chemoselective transformations, such as protonation alkylation. This protocol serves various from readily available amides.

Language: Английский

Citations

0
Substituent-Controlled Copper-Catalyzed Trifluoromethylation of 1,7-Dienes: Synthesis of Mono- and Bis-trifluoromethylated Benzoxepines DOI
Xiaowei Zhao, Xiang Gao,

Fangli Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7261 - 7266

Published: Aug. 21, 2024

A copper-catalyzed trifluoromethylation of benzene-linked 1,7-dienes with 1-trifluoromethyl-1,2-benziodoxole via a radical cascade cyclization process for the synthesis mono- and bis-trifluoromethylated benzoxepines is developed. The selectivity depends on substituents double bond allyl group in 1,7-dienes. large-scale operation late-stage functionalization bioactive molecules reveal promising utility this protocol.

Language: Английский

Citations

0
Making Full Use of TMSCF3: Deoxygenative Trifluoromethylation/Silylation of Amides DOI

Zhuzhu Zhang,

Lingling Chu

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(8), P. 2603 - 2603

Published: Jan. 1, 2024

Language: Английский

Citations

0