Aerobic conversion of organic halides to alcohols. An oxygenative radical cyclization

E Nakamura, T Inubushi, S Aoki…

Index: Nakamura, Eiichi; Inubushi, Tsuyoshi; Aoki, Satoshi; Machii, Daisuke Journal of the American Chemical Society, 1991 , vol. 113, # 23 p. 8980 - 8982

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Citation Number: 66

Abstract

Aerobic conversion of (E)-cinnamyl bromide (1) to cinnamyl alcohol (4) illustrates the simplicity and effectiveness of the reaction. Dry air was bubbled (1 20 mL/min) at 0 OC into a solution of 1 (1.97 g, 10.0 mmol) in 43 mL of toluene, to which Bu3SnH (6.1 1 g, 2 1. O mmol) was added dropwise. After air was bubbled in at 15-20 OC for 24 h, 0.1 g of NaBH4 in 1 mL of ethanol was added (to ensure reduction of 3). Purification of the crude productS on ...