The homoleptic lanthanide complex Sm[N(TMS)2]3 is an efficient rare-earth catalyst for the hydroboration of alkynes to the corresponding alkenylboron compounds. Practical applications were demonstrated in a gram-scale synthesis and further...
Lithium-promoted hydroboration of
alkynes and alkenes using commercially
available hexamethyldisilazane lithium as a precatalyst and HBpin
as a hydride source has been developed. This method will be appealing
for organic synthesis because of its remarkable substrate tolerance
and good yields. Mechanistic studies revealed that the hydroboration
proceeds through the in situ-formed BH3 species, which
acts to drive the turnover of the hydroboration of alkynes and alkenes.
Simple, commercially available iodine was successfully employed as a highly efficient and chemoselective catalyst for the oxidative annulation of β,γ-unsaturated hydrazones to produce 1,6-dihydropyridazines under mild conditions for the first time. Interestingly, when active β,γ-unsaturated hydrazone compounds containing electron-donating groups, such as furyl, thienyl, and cycloalkyl, were used, pyrroles were obtained. A gram-scale preparation experiment and further derivatization of pyridazines demonstrated the potential applicability of our synthesis method. Experimental studies and density functional theory calculations unveiled the origin of the chemoselectivity determining the formation of different products.
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