An efficient strategy involving electrochemical CC
double-bond
cleavage and functionalization of cyclic alkenes for the synthesis
of ketonitriles is described. This transformation features environmentally
friendly conditions and utilizes relatively safe TMSN3 as
the nitrogenation reagent and molecular oxygen as the oxidant. For
the open-chain alkenes, the reaction gave 1,2-difunctionalized products.
A wide range of cyclic alkenes and open-chain alkenes were found to
be compatible, providing the corresponding ketonitriles and α-azido
aromatic ketones in moderate to good yields.
A novel electrochemical cross-coupling method for the
synthesis
of thiocyanates via the direct cyanation of readily
available thiophenols or thiols with trimethylsilyl cyanide (TMSCN)
was developed. This approach was also suitable for selenols. External
oxidant-free, transition-metal-free and mild operating conditions
were the main advantages of this protocol. A series of thiocyanates
and selenocyanates could be obtained in moderate to high yields.
A practical electrochemical Minisci‐type reaction for the synthesis of silylated heterocycles is described. Using N‐hydroxyphthalimide (NHPI) as the hydrogen atom transfer (HAT) catalyst and trialkylsilanes as the silyl radical sources, a wide range of electron‐deficient heterocycles in‐cluding quinoline, quinoxaline, phthalazine, 3,6‐dichloropyridazine, phenanthridine, 6‐chloroimidazo[1,2‐b]pyridazine and coumarin, etc. were easily converted to the corresponding silylated products in 37–83% yields.
An efficient HOAc catalyzed three-component reaction of 2-(arylethynyl)anilines with arylaldehydes has been achieved, which lead to the generation of 3,3'-(arylmethylene)bis(1H-indoles) with good to excellent yields and high regioselectivity under transition-metal-free...
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