Cascade Photofragmentation/Photoalkylation for the Synthesis of α-Tertiary Alkyl Primary Amines

Key Points

This cascade synthesis effectively produces α-quaternary primary amines through n-h imine intermediates, showcasing a novel approach.
The method employs an efficient aza-norrish type ii fragmentation and subsequent photoalkylation under mild UV photocatalysis conditions.
One-pot reactions allow for the use of bench-stable phenacylamines, enhancing practical applications in organic chemistry.
Findings highlight the utility of photofragmentation, which remains relatively underexplored in synthesizing complex organic molecules.

Abstract

N-H imines are synthetically versatile but sensitive intermediates in organic synthesis. This work introduces a cascade synthesis of basic amines through N-H imine intermediates, featuring an efficient aza-Norrish Type II fragmentation, followed by photoalkylation. Our method selectively converts bench-stable phenacylamines to α-quaternary primary amines in one pot using mild and metal-free UV photocatalysis. Our work constitutes a rare use of amine photofragmentation in organic synthesis.

Bookmark

Cascade Photofragmentation/Photoalkylation for the Synthesis of α-Tertiary Alkyl Primary Amines

Key Points

Abstract

Cite This Study