Categories: CC Bond Formation >
Synthesis of haloalkynes
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Name Reactions
Recent Literature
Reaction of readily accessible benzylic and allylic alkyl bromides with iodoform
followed by a one-pot double elimination procedure enables a
triphenylphosphine-free synthesis of 1-iodoalkynes including facile purification
compared with Corey-Fuchs iodoalkynylation conditions. Replacing CHI3
with CHI2Cl allows the isolation of gem-(Z)-chloro-(E)-iodoalkenes.
The use of benzhydryl bromides as nucleophiles leads to trisubstituted alkenes.
G. Pelletier, S. Lie, J. J. Mousseau, A. B. Charette, Org. Lett., 2012,
14, 5464-5467.
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.
M. Okutani, Y. Mori, J. Org. Chem., 2009,
74, 442-444.
Deprotonation of 3,3,3-trichloropropyl-1-triphenylphosphonium chloride
generates the corresponding phosphorane, which reacts with aldehydes to give
trichloromethylated (Z)-olefins, which are useful for the synthesis
of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes
in high yields and stereospecificities.
M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc.,
2004, 126, 14314-14315.