The Barbier-type alkylation of aldehydes with alkyl halides in the presence of metallic strontium

N Miyoshi, K Kamiura, H Oka, A Kita, R Kuwata…

Index: Miyoshi, Norikazu; Kamiura, Koji; Oka, Hiromi; Kita, Akiko; Kuwata, Rika; Ikehara, Daitetsu; Wada, Makoto Bulletin of the Chemical Society of Japan, 2004 , vol. 77, # 2 p. 341 - 345

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Citation Number: 6

Abstract

In the presence of metallic strontium, the Barbier-type alkylation of aldehydes with alkyl iodides proceeded smoothly at− 15° C under an argon atmosphere to afford the corresponding alkylated alcohols in moderate to good yields. The unusual addition reaction of ethyl benzoate with tert-butyl iodide took place to give the p-tert-butylated alkylated product (the 1, 6-adduct of the benzoate) in 55% yield. Using strontium isopropoxide, the ...