A simple and efficient radical reduction using water-soluble radical initiator and hypophosphorous acid in aqueous alcohol

• Published in: Tetrahedron letters Vol. 45; no. 48; pp. 8927 - 8929
• Main Authors: Nambu, Hisanori, Alinejad, Anahita Hessamian, Hata, Kayoko, Fujioka, Hiromichi, Kita, Yasuyuki
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.11.2004; Elsevier
• Subjects: Aqueous alcohol; Chemistry; Chemistry, Organic; Hypophosphorous acid; Physical Sciences; Radical reduction; Science & Technology; The water-soluble radical initiator; Radical reduction; Hypophosphorous acid; Aqueous alcohol; The water-soluble radical initiator; hypophosphorous acid; BOND-FORMING REACTION; N-ETHYLPIPERIDINE HYPOPHOSPHITE; METHODOLOGY; OXIDE; aqueous alcohol; radical reduction; DEOXYGENATION; DEHALOGENATION; the water-soluble radical initiator; CYCLIZATION
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2004.09.130

A simple, mild and high-yielding procedure for the reduction of various halogenated compounds using a combination of the water-soluble radical initiater (VA-061), hypophosphorous acid and triethylamine in aqueous alcohol is reported. A simple, mild, and high-yielding procedure for the reduction of various halogenated compounds using a combination of the water-soluble radical initiator, 2,2′-azobis[2-(2-imidazolin-2-yl)propane] (VA-061), a water-soluble chain carrier, hypophosphorous acid, and the base, triethylamine, in aqueous alcohol is described. The reagents used in this method are all water soluble, and therefore, an almost pure desired product can be readily obtained using only an extraction procedure.