Catalyst-free decarboxylative deuteration using tailored photoredox-active carboxylic acids

Achieving precise deuterium labeling in pharmaceutical compounds presents a formidable challenge in medicinal chemistry. Herein, we introduce an innovative approach for circumventing the use of costly and environmentally unfriendly photocatalysts, enabling precise decarboxylative deuteration under m...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2024-10, Vol.26 (2), p.1456-1462
Main Authors: Liu, Shuai, Liao, Hongze, Chen, Bin, Guo, Tengyu, Zhang, Zhizhen, Lin, Houwen
Format: Article
Language:English
Subjects:
Alkanes
Amines
Carboxylic acids
Catalysts
Deuteration
Deuterium
Medical innovations
Natural products
Peptides
Photosensitivity
Terpenes
Transition metals
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Summary:Achieving precise deuterium labeling in pharmaceutical compounds presents a formidable challenge in medicinal chemistry. Herein, we introduce an innovative approach for circumventing the use of costly and environmentally unfriendly photocatalysts, enabling precise decarboxylative deuteration under mild conditions. Mechanistic investigation unveils the dual functionality of the tailored photoredox-active acid (PAC) with a photosensitive amino protecting group, serving both as a reactant and as a catalyst. This methodology not only represents a sustainable solution, eliminating the need for additional transition-metal catalysts, but also showcases exceptional regio- and chemoselectivity, successfully producing a versatile range of deuterated amines and alkanes, including complex peptides, terpenoids, and steroidal natural products. This breakthrough marks a significant advancement in the realm of photoinduced autocatalytic reaction methodologies. Herein, we introduce a green, catalyst-free method for precise decarboxylative deuteration using tailored photoredox-active acid (PAC) under mild conditions. Mechanistic investigations reveal that PAC simultaneously acts as both reactant and catalyst.
ISSN:1463-9262
1463-9270
DOI:10.1039/d4gc01134a