A nickel-catalyzed
decarbonylative thioetherification of carboxylic
acids with thiols was developed. Under the reaction conditions, benzoic
acids, cinnamic acids, and benzyl carboxylic acids coupled with various
thiols including both aromatic and aliphatic ones produce the corresponding
thioethers in up to 99% yields. Moreover, this reaction was applicable
to the modification of bioactive molecules such as 3-methylflavone-8-carboxylic
acid, probenecid, and flufenamic acid, and the synthesis of acaricide
chlorbenside. These results well demonstrated the potential synthetic
value of this new reaction in organic synthesis.
The direct decarbonylative cyanation of benzoic acids
with TMSCN
was achieved through palladium catalysis. By this strategy, a wide
range of nitriles including those with functional groups was synthesized
in good to high yields. Moreover, this reaction applied to modifying
bioactive molecules such as adapalene, probenecid, telmisartan, and
3-methylflavone-8-carboxylic acid. These results demonstrate that
this new reaction has potential synthetic value in organic synthesis.
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