Electroreductive Cross-Coupling between Aromatic Aldehydes and Chlorosilanes Enabling the Synthesis of α-Silyl Alcohols DOI

Fen Han,

Qian Su,

Yu Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 7037 - 7042

Published: Aug. 14, 2024

α-Silyl alcohols are powerful structural motifs for pharmaceutical chemistry, materials and organic synthesis. The limitations of current synthetic techniques encompass a requirement difficult-to-obtain silyl precursors, noble-metal catalysts, narrow substrate scopes. Here, we developed general method α-silyl through electroreductive cross-coupling aldehydes chlorosilane. This features easily available reagents, mild conditions, wide scope. establishment this protocol will provide an alternative access to alcohols.

Language: Английский

Multistep Cascade Catalyzed by a Single-Chiral Lewis Acid: Efficient Asymmetric Synthesis of Macrocyclic Chiral Dilactones and Dilactams DOI Creative Commons
Bailin Wang,

Jie-Qiang Yu,

Qian Zhang

et al.

JACS Au, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

Language: Английский

Citations

0
Synthesis of Oxazoles Containing CF3-Substituted Alcohol Unit via Tandem Cycloisomerization/Hydroxyalkylation from N-Propargylamides with Trifluoropyruvates DOI Creative Commons
Juanjuan Gao,

Longhui Wu,

Shuqin Yu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(24), P. 5848 - 5848

Published: Dec. 11, 2024

Oxazoles are important five-membered heterocycles that contain both nitrogen and oxygen atoms. Due to their wide range of biological activities, many oxazoles demonstrate potential for extensive application in various fields, including medicinal chemistry. Trifluoromethyl carbinol, an pharmacophore, contains trifluoromethyl hydroxyl groups is common molecules with activities. Constructing a carbinol unit undoubtedly valuable expanding the chemical space drug discovery. In this study, simple efficient method was developed synthesis containing CF3-substituted alcohol via tandem cycloisomerization/hydroxyalkylation N-propargylamides trifluoropyruvates through rational Lewis acid catalytic mechanism. This Zn(OTf)2-catalyzed synthetic protocol operationally provides series moderate good yields. The demonstrates broad substrate scope, high functional group tolerance, atom economy can achieve gram-level reactions, indicating strong possibility its practical application.

Language: Английский

Citations

1
Stereodivergent Assembly of δ-Valerolactones with an Azaarene-Containing Quaternary Stereocenter Enabled by Cu/Ru Relay Catalysis DOI Creative Commons

Kui Tian,

Z.‐T. JIN,

Xin‐Lian Liu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 3, 2024

Stereodivergent synthesis of chiral δ-valerolactones bearing a unique azaarene-containing α-quaternary and tertiary stereocenter was enabled by Cu/Ru relay catalysis via cascade borrowing hydrogen/Michael addition/lactonization protocol.

Language: Английский

Citations

0
Electroreductive Cross-Coupling between Aromatic Aldehydes and Chlorosilanes Enabling the Synthesis of α-Silyl Alcohols DOI

Fen Han,

Qian Su,

Yu Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 7037 - 7042

Published: Aug. 14, 2024

α-Silyl alcohols are powerful structural motifs for pharmaceutical chemistry, materials and organic synthesis. The limitations of current synthetic techniques encompass a requirement difficult-to-obtain silyl precursors, noble-metal catalysts, narrow substrate scopes. Here, we developed general method α-silyl through electroreductive cross-coupling aldehydes chlorosilane. This features easily available reagents, mild conditions, wide scope. establishment this protocol will provide an alternative access to alcohols.

Language: Английский

Citations

0