Synthesis of\nβ‑Silyl Amines via Merging\nPhotoinduced Energy and Hydrogen Atom Transfer in Flow

The development of efficient methods for synthesizing\nβ-silyl\namines has long been a significant goal in organic synthesis. Previous\nmethods mainly relied on the use of prefunctionalized substrates or\nspecial reagents. Herein, we present a visible-light-promoted synthesis\napproach for β-silyl amines, utilizing a combination of photoinduced\nenergy and hydrogen atom transfer processes. Using flow chemistry\ntechnology, a variety of valuable skeletons, including β-silyl\namines and α-amino esters, can be produced from readily available\nfeedstocks such as hydrosilanes and simple alkanes. Moreover, the\nstrategy’s full-process fluidized production capability highlights\nits potential for industrial-scale manufacturing. Mechanistic studies\nrevealed that oxime esters can act as radical precursors as well as\nhydrogen atom transfer reagents.

Publication Details

Journal
Figshare
Published
2024-09-30
DOI
https://doi.org/10.1021/acs.orglett.4c02998.s001
Primary Topic
Innovative Microfluidic and Catalytic Techniques Innovation
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article
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article

Synthesis of\nβ‑Silyl Amines via Merging\nPhotoinduced Energy and Hydrogen Atom Transfer in Flow

Figshare
Innovative Microfluidic and Catalytic Techniques Innovation
article

Synthesis of\nβ‑Silyl Amines via Merging\nPhotoinduced Energy and Hydrogen Atom Transfer in Flow

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Abstract

The development of efficient methods for synthesizing\nβ-silyl\namines has long been a significant goal in organic synthesis. Previous\nmethods mainly relied on the use of prefunctionalized substrates or\nspecial reagents. Herein, we present a visible-light-promoted synthesis\napproach for β-silyl amines, utilizing a combination of photoinduced\nenergy and hydrogen atom transfer processes. Using flow chemistry\ntechnology, a variety of valuable skeletons, including β-silyl\namines and α-amino esters, can be produced from readily available\nfeedstocks such as hydrosilanes and simple alkanes. Moreover, the\nstrategy’s full-process fluidized production capability highlights\nits potential for industrial-scale manufacturing. Mechanistic studies\nrevealed that oxime esters can act as radical precursors as well as\nhydrogen atom transfer reagents.

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