Catalyzed addition of acid chlorides to alkynes by unmodified nano-powder magnetite: synthesis of chlorovinyl ketones, furans, and related cyclopentenone derivatives

摘要: Abstract Inexpensive and commercially available nano-powder magnetite is an excellent catalyst for the addition of acid chlorides to internal terminal alkynes, yielding corresponding chlorovinyl ketones in good yields. The process has been applied synthesis 5-chloro-4-arylcyclopent-2-enones, 3-aryl-1H-cyclopenta[a]naphthalen-1-ones, (E)-3-alkylidene-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ones, just by changing nature starting chloride or alkyne. All tested processes elapse with acceptable regio- stereo-selectivity. Moreover, use iridium impregnated on permits integration chloroacylation a second dehydrochlorination–annulation yield, one-pot, 1-aryl-2,4-dialkylfurans yields, independently reagents, including heteroaromatic ones.