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Low-Valent Titanium-Mediated Radical Conjugate Addition Using Benzyl Alcohols as Benzyl Radical Sources

Takuya Suga*, Shoma Shimazu, Yutaka Ukaji*

*Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan, Email: suga-tse.kanazawa-u.ac.jp, ukajistaff.kanazawa-u.ac.jp

T. Suga, S. Shimazu, Y. Ukaji, Org. Lett., 2018, 20, 5389-5392.

DOI: 10.1021/acs.orglett.8b02305 (free Supporting Information)


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Abstract

The simple and inexpensive combination of TiCl4(2,4,6-collidine) and manganese powder afforded a low-valent titanium reagent, which facilitated homolytic cleavage of benzylic C-OH bonds. Radical conjugate addition reactions of various benzyl alcohol derivatives with electron-deficient alkenes furnished the corresponding adducts in good yields.


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Key Words

benzylation, nitriles


ID: J54-Y2018