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- W3003325372 endingPage "3644" @default.
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- W3003325372 abstract "In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl–ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl–ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates." @default.
- W3003325372 created "2020-02-07" @default.
- W3003325372 creator A5023229525 @default.
- W3003325372 creator A5023473958 @default.
- W3003325372 creator A5030575747 @default.
- W3003325372 creator A5037699390 @default.
- W3003325372 creator A5066680838 @default.
- W3003325372 creator A5078639364 @default.
- W3003325372 date "2020-01-31" @default.
- W3003325372 modified "2023-10-14" @default.
- W3003325372 title "Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl–Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines" @default.
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