期刊
ACS CATALYSIS
卷 11, 期 5, 页码 3153-3158出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c00099
关键词
photoredox; organic; catalysis; heterocycle; dehydrogenation; anti-Markovnikov
资金
- Alkermes, Inc.
- NIGMS [1R35GM136330-01]
The direct beta-functionalization of saturated aza-heterocycles has been a challenge due to the nature of beta-C-H bonds. The study demonstrates a successful beta-functionalization approach enabled by a two-step organic photoredox catalysis method, involving copper-mediated dehydrogenation followed by hydrofunctionalization of ene-carbamates. The reaction provides a range of C-C, C-O, and C-N aza-heterocycles at the beta-position.
The direct beta-functionalization of saturated aza-heterocycles has remained a synthetic challenge because of the remote and unactivated nature of beta-C-H bonds in these motifs. Herein, we demonstrate the beta-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 beta-position.
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