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ID 117576
著者
Mihara, Tomohiro Tokushima University
Fujii, Hiroki Tokushima University
資料タイプ
学術雑誌論文
抄録
We present that thioacetalization of aldehydes can be induced by blue light irradiation in the presence of a catalytic amount of riboflavin tetraacetate (RFTA) under aerobic conditions. Several control experiments have suggested that the reaction is more likely to be catalyzed by acidic species generated in situ during the light irradiation. We have proposed that single electron transfer from a thiol (RSH) to the excited state of RFTA can take place to give a one-electron oxidized thiol (RSH+•) and the one-electron reduced RFTA (RFTA–•), which can be trapped by molecular oxygen to be stabilized as Brønsted acids including the protonated RFTA–• (RFTAH•). Finally, we have demonstrated that such acidic species can be prepared in advance as a solution and used as Brønsted acid catalysts for not only the thioacetalization but also Mannich-type reactions.
掲載誌名
Chemical Communications
ISSN
1364548X
cat書誌ID
AA11071130
AA12455105
出版者
The Royal Society of Chemistry
56
42
開始ページ
5661
終了ページ
5664
発行日
2020-04-09
EDB ID
出版社版DOI
出版社版URL
フルテキストファイル
言語
eng
著者版フラグ
著者版
部局
理工学系
教養教育院