Sunlight-induced CC bond formation reaction: Radical addition of alcohols/ethers/acetals to olefins

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2021-05, Vol.413, Article 113263
• Main Authors: Hayakawa, Mamiko, Shirota, Hisashi, Hirayama, Souta, Yamada, Ryuusei, Aoyama, Tadashi, Ouchi, Akihiko
• Format: Article
• Language: English
• Subjects: Acetal; Alcohol; C[sbnd]C bond formation; Ether; Olefin; Sunlight
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2021.113263

[Display omitted] •Sunlight induced CC bond formation reaction proceeded efficiently.•Addition of alcohols/ethers/acetals to olefins proceeded using t-Bu2O2.•The reactions are completed mostly within 3–4 h at room temperature in > 95 % yield.•Gram-scale reactions proceeded efficiently without large extention of reaction time. A sunlight-induced CC bond formation reactions upon the addition of alcohols/ethers/acetals to olefins proceeded efficiently using di-tert-butyl peroxide (DTBP). The reactions proceeded faster than many of the previously reported sunlight and many conventional lamp photolyses, typically in 3–4 h under irradiation with sunlight, in excellent yield using olefins bearing two electron withdrawing groups (EWGs) (product yield > 95 %) and in good to fair yield with olefins bearing one EWG. The yields observed for some products were ∼20 % higher than those obtained using a conventional Xe lamp as the light source, which was confirmed to be due to a light intensity effect. Gram-scale experiments showed similar yields to those observed in their corresponding small-scale experiments.