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Organic Dye‐Photocatalyzed Acylnitroso Ene Reaction
Author(s) -
Teo Yew Chin,
Pan Yuanhang,
Tan Choon Hong
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200435
Subject(s) - rose bengal , ene reaction , chemistry , allylic rearrangement , photochemistry , singlet oxygen , amination , catalysis , quenching (fluorescence) , photoredox catalysis , environmentally friendly , intermolecular force , fluorescence , oxygen , organic chemistry , photocatalysis , molecule , ecology , physics , quantum mechanics , biology
Rose bengal, an inexpensive and readily available organic dye, is demonstrated to be a photoredox catalyst for the formation of transient acylnitroso intermediates under visible light irradiation. This method is operationally simple and uses air as the terminal oxidant. Reactions of acylnitroso with a range of functionalized alkenes give intermolecular acylnitroso ene products in moderate to good yields. This is an environmentally friendly allylic amination methodology that avoids the use of metal catalysts and stoichiometric amount of oxidants. A plausible reaction mechanism is proposed on the basis of singlet oxygen and fluorescence quenching studies.