ortho‐Alkylation of Pyridine N‐Oxides with Alkynes by Photocatalysis: Pyridine N‐Oxide as a Redox Auxiliary
JP Markham, B Wang, ED Stevens… - … A European Journal, 2019 - Wiley Online Library
Chemistry–A European Journal, 2019•Wiley Online Library
A photocatalyzed ortho‐alkylation of pyridine N‐oxide with ynamides and arylacetylenes
has been developed, which yields a series of α‐(2‐pyridinyl) benzyl amides/ketones.
Mechanistic studies, including electrochemical studies, radical‐trapping experiments, and
Stern–Volmer fluorescence quenching studies demonstrate that pyridine N‐oxide serves as
both a redox auxiliary and radical acceptor to achieve the mild photocatalytic single‐electron
oxidation of carbon–carbon triple bonds with the generation of a cationic vinyl radical …
has been developed, which yields a series of α‐(2‐pyridinyl) benzyl amides/ketones.
Mechanistic studies, including electrochemical studies, radical‐trapping experiments, and
Stern–Volmer fluorescence quenching studies demonstrate that pyridine N‐oxide serves as
both a redox auxiliary and radical acceptor to achieve the mild photocatalytic single‐electron
oxidation of carbon–carbon triple bonds with the generation of a cationic vinyl radical …
Abstract
A photocatalyzed ortho‐alkylation of pyridine N‐oxide with ynamides and arylacetylenes has been developed, which yields a series of α‐(2‐pyridinyl) benzyl amides/ketones. Mechanistic studies, including electrochemical studies, radical‐trapping experiments, and Stern–Volmer fluorescence quenching studies demonstrate that pyridine N‐oxide serves as both a redox auxiliary and radical acceptor to achieve the mild photocatalytic single‐electron oxidation of carbon–carbon triple bonds with the generation of a cationic vinyl radical intermediate.
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