Triethylborane-induced hydrodehalogenation of organic halides by tin hydrides.

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概要

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• 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 nonstereospecifically. (3) The reduction of aryl halides with <I>n</I>-Bu<SUB>3</SUB>SnH–Et<SUB>3</SUB>B system was not so effective as the reduction of alkyl halides and alkenyl halides. Whereas aryl iodides were reduced at room temperature with <I>n</I>-Bu<SUB>3</SUB>SnH, aryl bromides hardly reacted with <I>n</I>-Bu<SUB>3</SUB>SnH even at 80 °C.

• 公益社団法人 日本化学会の論文

著者

• Nozaki Kyoko

  Department Of Applied Physics Defence Academy

• Fugami Keigo

  Department Of Applied Chemistry Faculty Of Engineering Nagasaki University

• Miura Katsukiyo

  Department Of Applied Chemistry Graduate School Of Science And Engineering Saitama University

• Utimoto Kiitiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Oshima Koichiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Ichinose Yoshifumi

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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