Synthesis of Elongated Esters from Alkenes

A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible‐light irradiation of an ester‐stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon–...

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Veröffentlicht in:	Angewandte Chemie International Edition 2018-11, Vol.57 (47), p.15455-15459
Hauptverfasser:	Miura, Tomoya, Funakoshi, Yuuta, Nakahashi, Junki, Moriyama, Daisuke, Murakami, Masahiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Aliphatic compounds Alkenes Carbon Elongation Esters Irradiation Light irradiation Methyl radicals Phosphorus photocatalysis Radiation radicals ylides
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Beschreibung
Zusammenfassung:	A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible‐light irradiation of an ester‐stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon–carbon double bond of an alkene to produce an elongated aliphatic ester. Stretching out: A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible‐light irradiation of an ester‐stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical adds to the carbon–carbon double bond of an alkene to produce an elongated aliphatic ester. ppy=2‐phenylpyridinato.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201809115