Triethylborane-induced hydrodehalogenation of organic halides by tin hydrides.

…, Y Ichinose, K Nozaki, K Fugami, K Oshima…

Index: Miura, Katsukiyo; Ichinose, Yoshifumi; Nozaki, Kyoko; Fugami, Keigo; Oshima, Koichiro; Utimoto, Kiitiro Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 1 p. 143 - 147

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Citation Number: 174

Abstract

The reduction of organic halides with tributyltin hydride in the presence of a catalytic amount of triethylborane has been studied.(1) Alkyl iodides and alkyl bromides reacted easily with tin hydride at− 78° C to give the corresponding hydrocarbons, while alkyl chlorides were sluggish to react and recovered unchanged.(2) The reduction of alkenyl halides such as 1- deuterio-1-iodo-1-dodecene and 1-iodo-1-triethylsilyl-1-dodecene proceeded ...