Site-Selective O-Arylation of Carbohydrate Derivatives through Nickel–Photoredox Catalysis

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Site-selective O-arylations of glycoside-derived diols have been achieved by couplings with bromoarenes upon irradiation blue LEDs in the presence an iridium photocatalyst and a nickel complex. The use hexamethylenetetramine (hexamine) place quinuclidine, along application methoxy-substituted 2,2′-bipyridine ligand, provided improvements yield for this relatively challenging substrate class. Selective arylation took at less sterically hindered OH group, as determined substitution pattern configuration glycoside substrate. Percent buried volume calculations were used to quantify relative levels steric hindrance two reactive sites.

Language: Английский

Organometallic Photocatalyst‐Promoted Synthesis and Modification of Carbohydrates under Photoirradiation

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 27, 2024

Carbohydrates are natural, renewable, chemical compounds that play crucial roles in biological systems. Thus, efficient and stereoselective glycosylation is an urgent task for the preparation of pure structurally well-defined carbohydrates. Photoredox catalysis has emerged as a powerful tool carbohydrate chemistry, providing alternative addressing some challenges glycochemistry. Over last few decades, Ir- Ru-based organometallic photocatalysts have attracted significant interest because their high stability, high-energy triplet state, strong visible-light absorption, long luminescence lifetime, amenability to ligand modification. This review highlights recent progress photocatalyst-promoted synthesis modification carbohydrates under photoirradiation, well related benefits drawbacks.

Language: Английский