β‑Functionalization of Saturated Aza-Heterocycles Enabled by Organic Photoredox Catalysis

β‑Functionalization of Saturated Aza-Heterocycles Enabled by Organic Photoredox Catalysis

The direct β-functionalization of saturated aza-heterocycles has remained a synthetic challenge because of the remote and unactivated nature of β-C–H bonds in these motifs. Herein, we demonstrate the β-functionalization of saturated aza-heterocycles enabled by a two-step organic photoredox catalysis...

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Bibliographic Details
Published in:ACS catalysis Vol. 11; no. 5; pp. 3153 - 3158
Main Authors: Holmberg-Douglas, Natalie, Choi, Younggi, Aquila, Brian, Huynh, Hoan, Nicewicz, David A
Format: Journal Article
Language:English
Published: American Chemical Society 05-03-2021
Subjects:
catalysis
dehydrogenation
photoredox
heterocycle
organic
anti-Markovnikov
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Summary:The direct β-functionalization of saturated aza-heterocycles has remained a synthetic challenge because of the remote and unactivated nature of β-C–H bonds in these motifs. Herein, we demonstrate the β-functionalization of saturated aza-heterocycles enabled by a two-step organic photoredox catalysis approach. Initially, a photoredox-catalyzed copper-mediated dehydrogenation of saturated aza-heterocycles produces ene-carbamates. This is followed by an anti-Markovnikov hydrofunctionalization of the ene-carbamates with a range of heteroatom-containing nucleophiles furnishing an array of C–C, C–O, and C–N aza-heterocycles at the β-position.
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ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c00099