Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis

A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N‐protected 1‐aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac‐[Ir(ppy)3] and [Ir(ppy)2(dtbbpy)](PF6) (ppy=2‐pyridylphenyl, d...

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Bibliographic Details
Published in:Chemistry : a European journal 2015-08, Vol.21 (33), p.11677-11680
Main Authors: Miyazawa, Kazuki, Koike, Takashi, Akita, Munetaka
Format: Article
Language:English
Subjects:
amination
carbocations
Catalysis
Chemistry
Derivatives
electron transfer
homogeneous catalysis
Olefins
Photocatalysis
Photocatalysts
photochemistry
Precursors
Radicals
Synthesis
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Summary:A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N‐protected 1‐aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac‐[Ir(ppy)3] and [Ir(ppy)2(dtbbpy)](PF6) (ppy=2‐pyridylphenyl, dtbbpy=4,4′‐di‐tert‐butyl‐2,2′‐bipyridine). The present photocatalytic system allows for synthesis of vicinal aminoalcohol derivatives from olefins with various functional groups under mild reaction conditions with easy handling. Protect ya N: A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N‐Protected 1‐aminopyridinium salts serve as amidyl radical precursors by the action of Ir photocatalysts, fac‐[Ir(ppy)3] and [Ir(ppy)2(dtbbpy)]+ (ppy=2‐pyridylphenyl, dtbbpy=4,4′‐di‐tert‐butyl‐2,2′‐bipyridine). The present photocatalytic system allows easy synthesis of 1,2‐aminoalcohol derivatives from olefins with various functionalities.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201501590