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Conversion of Bromoalkenes into Alkynes by Wet Tetra-n-butylammonium Fluoride

Masaru Okutani and Yuji Mori*

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan, Email:

M. Okutani, Y. Mori, J. Org. Chem., 2009, 74, 442-444.

DOI: 10.1021/jo802101a


Tetra-n-butylammonium is a mild and efficient base for the elimination of bromoalkenes. Treatment of 1,1-dibromoalkenes, (Z)-1-bromoalkenes, and internal bromoalkenes with 5 equiv of TBAF • 3 H2O in DMF yielded terminal and internal alkynes in high yields without problems regarding the presence of water.

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Key Words

bromoalkynes, internal alkynes, terminal alkynes

ID: J42-Y2009-0150