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

Organic Letters
Takuya SugaYutaka Ukaji

Abstract

A concise method to directly generate benzyl radicals from benzyl alcohol derivatives has been developed. The simple and inexpensive combination of TiCl4(collidine) (collidine = 2,4,6-collidine) and manganese powder afforded a low-valent titanium reagent, which facilitated homolytic cleavage of benzylic C-OH bonds. The application to radical conjugate addition reactions demonstrated the broad scope of this method. The reaction of various benzyl alcohol derivatives with electron-deficient alkenes furnished the corresponding radical adducts.

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Citations

Jan 10, 2019·Chemistry : a European Journal·Jia-Bin HanXiang-Ying Tang
Apr 6, 2019·Organic & Biomolecular Chemistry·Yingying PanHegui Gong

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