Synthesis of γ-amino acids via photoinduced hydrocarboxylation of allylamines

06 September 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we disclose a new photochemical process to prepare γ-amino acids from allylamines and formic acid salts. The investigated redox-neutral hydrocarboxylation process produces high yields across a wide range of functionalized allylamine substrates with excellent regioselectivity. The developed operationally simple protocol can be readily scaled with low photocatalyst loading (from 1% up to 0.02 mol%) without the need for any precautions to exclude air or moisture. The mechanistic working model utilizes a thiol-catalyzed radical chain process, delivering the hydrogen atom and CO2 from formate across the alkene substrate through the carboxylate radical (CO2•-), a crucial reactive intermediate

Keywords

allylamines
γ-amino acids
hydrocarboxylation
photocatalysis
hydrofunctionalization

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