Stereoselective addition reactions of
in situ generated XX’ (IBr, BrCl) and HX (X =Cl, Br, I) to alkynes are described. The
in situ XX’ were found to effectively occur from mixing up of commercially available halotrimethylsilane (TMSX) with
N-halosuccinimide (NX’S). The
in situ BrCl effectively bonded to silylethynylarenes in complete
syn-fashion, and the
in situ IBr reacted with internal aliphatic alkynes and ynamides in
anti-mode; these afforded perfect formation of single isomers. The resultant bis-halogenated alkenes can be reasonably multi-tunable templates for synthesis of differentially all-carbon tetrasubstituted olefins. In a similar vein, the
in situ HX generated from TMSX and H
2O undertook stereoselective addition of alkynes, which gave synthetically mono-halogenated scaffolds for preparing trisubstitued olefins and disubstituted
exo-methylenes. It thus provided a potentially diverse scaffold for differently poly-substituted olefins.
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