Recent Progress in Haloalkene Synthesis by Hydrohalogenation (HX=HCl, HBr, HI) of Alkynes
Kento Iwai,
Nagatoshi Nishiwaki
Abstract:Hydrohalogenation of alkynes is one of the fundamental reactions in organic chemistry, as described in textbooks that begins from old time as Reppe’s chemistry. This method, which directly affords haloalkenes in a single step, is attractive from both industrial and academic viewpoints. Despite the long history of this reaction, novel efficient catalysts and regioselective and/or stereoselective controlled reactions are still a challenging topic. This review addresses the recent (past decade) advances in this f… Show more
SCF 3 -substituted internal alkynes undergo regio-and stereoselective hydrohalogenation to provide the corresponding β-halo-α-SCF 3 -alkenes. The regioselectivity is ensured by the strong polarization of the C�C triple bond in SCF 3 -alkynes, while the stereoselectivity is governed by the strength of the proton donor and/or by the solvent polarity. The potential of β-iodo-α-SCF 3alkenes was illustrated in several cross-coupling, protodeiodination, and cyanation reactions.
SCF 3 -substituted internal alkynes undergo regio-and stereoselective hydrohalogenation to provide the corresponding β-halo-α-SCF 3 -alkenes. The regioselectivity is ensured by the strong polarization of the C�C triple bond in SCF 3 -alkynes, while the stereoselectivity is governed by the strength of the proton donor and/or by the solvent polarity. The potential of β-iodo-α-SCF 3alkenes was illustrated in several cross-coupling, protodeiodination, and cyanation reactions.
The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithum halocarbenoids is reported. Upon forming the corresponding tetrahedral intermediate adduct, followed by...
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