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γ-Butyrolactone Synthesis from Allylic Alcohols Using the CO_(2)Radical Anion

Precision Chemistry 2024年第3期2卷 88-95页

作者： Saeesh R.Mangaonkar Hiroki Hayashi Wataru Kanna suvankar debbarma Yu Harabuchi Satoshi Maeda Tsuyoshi Mita Institute for Chemical Reaction Design and Discovery(WPI-ICReDD) Hokkaido UniversitySapporoHokkaido 001-0021Japan JST ERATO Maeda Artificial Intelligence in Chemical Reaction Design and Discovery ProjectSapporoHokkaido 060-0810Japan Department of Chemistry Faculty of ScienceHokkaido UniversitySapporoHokkaido 060-0810Japan Research and Services Division of Materials Data and Integrated System(MaDIS) National Institute for Materials Science(NIMS)TsukubaIbaraki 305-0044Japan

γ-Butyrolactone structures are commonly found in various natural products and serve as crucial building blocks in organic ***,the development of methods for synthesizingγ-butyrolactones has garnered significant interest within the organic synthesis *** this study,we present a direct and highly efficient approach for the synthesis ofγ-butyrolactones from allylic ***,this study represents the first instance ofγ-butyrolactone synthesis initiated by radical hydrocarboxylation using CO_(2)^(•–),generated from metal formates,followed by *** two-step process is achieved through the synergistic interaction of photoredox and hydrogen atom transfer(HAT)catalysis,resulting in the production ofγ-butyrolactones with exceptional ***,when employingα,α-diaryl allylic alcohol derivatives as substrates,the reaction involves 1,2-aryl migration,which occurs concomitantly with CO_(2)^(•–)addition,leading to the formation of 4,5-substituted lactones in a good *** artificial force induced reaction(AFIR)method identified the preferred 1,2-aryl migration pathway along with potential byproduct pathways,in which the targeted 1,2-migration was found to be the most plausible pathway.

关键词： CO_(2) lactone radical photoredox visible light carboxylation calculation DFT

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