Metallaphotoredox deuteroalkylation utilizing thianthrenium salts

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Medicinal Chemistry

Background:

• Deuterium labeling is vital in organic and pharmaceutical chemistry.
• Current synthesis of deuterated compounds relies on limited deuterated building blocks.
• Lack of efficient synthetic routes to deuterated synthons hinders progress.

Purpose of the Study:

• To present a novel method for efficient and selective deuterium incorporation.
• To utilize alkyl-substituted thianthrenium salts for α-deuteration.
• To enable the synthesis of diverse deuterium-labeled compounds.

Main Methods:

• Employed pH-dependent hydrogen isotope exchange (HIE) using D2O.
• Utilized alkyl-substituted thianthrenium salts as key reagents.
• Demonstrated compatibility with metallaphotoredox cross-electrophile coupling reactions.

Main Results:

• Achieved selective deuterium incorporation at the α position of alkyl chains.
• Generated α-deuterated alkyl thianthrenium salts with high deuterium content.
• Showcased broad substrate scope and precise control over deuterium insertion sites.

Conclusions:

• The developed method provides a versatile tool for synthesizing deuterium-labeled compounds.
• This approach is particularly valuable for pharmaceutical research and development.
• Offers precise control over deuterium labeling in complex molecules.