有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
ドミノ型ラジカル閉環反応の開発研究
宮部 豪人吉岡 英斗甲谷 繁
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2015 年 73 巻 9 号 p. 895-901

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This article highlights our recent studies on radical chemistry using the domino reactions constructing the carbon-carbon and carbon-heteroatom bonds. Stereocontrol in domino radical addition-cyclization-trapping reactions was achieved by new approach, which contains hydroxamate ester moiety as a chiral Lewis acid-coordinating tether between two radical acceptors. The polarity-mismatched perfluoroalkyl radical addition was next studied. The domino reaction with perfluoroalkyl radicals proceeded via the unfavorable polarity-mismatched addition of electrophilic radicals to electron-deficient acceptors. The photo-induced domino reactions were also studied in aqueous media. The photocatalyst, Ru(bpy)3Cl2·6H2O, has the potential to induce the carbon-carbon bond-forming reactions in aqueous media. In the presence of water, the photo-induced electron transfer (PIET) from the excited singlet state of rhodamine B smoothly proceeded and promoted domino reactions.

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