72457-25-1Relevant articles and documents
A heavy-metal-free desulfonylative Giese-type reaction of benzothiazole sulfones under visible-light conditions
Inuzuka, Toshiyasu,Iwama, Haruka,Ogawa, Daichi,Sengoku, Tetsuya,Yoda, Hidemi
supporting information, p. 9858 - 9861 (2021/10/12)
A visible-light-induced desulfonylative Giese-type reaction has been developed. Essential to the success is the employment of Hantzsch ester to activate benzothiazole sulfones without any heavy-metal additives. Not only benzylic benzothiazole sulfones but also alkyl ones were viable substrates and reacted with electron-deficient alkenes and a propiol amide.
Coupling Photocatalysis and Substitution Chemistry to Expand and Normalize Redox-Active Halides
Rathnayake, Manjula D.,Weaver, Jimmie D.
supporting information, p. 2036 - 2041 (2021/04/05)
Photocatalysis can generate radicals in a controlled fashion and has become an important synthetic strategy. However, limitations due to the reducibility of alkyl halides prevent their broader implementation. Herein we explore the use of nucleophiles that can substitute the halide and serve as an electron capture motif that normalize the variable redox potentials across substrates. When used with photocatalysis, bench-stable, commercially available collidinium salts prove to be excellent radical precursors with a broad scope.
Low-Valent Titanium-Mediated Radical Conjugate Addition Using Benzyl Alcohols as Benzyl Radical Sources
Suga, Takuya,Shimazu, Shoma,Ukaji, Yutaka
supporting information, p. 5389 - 5392 (2018/09/12)
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.