1260246-19-2

Upstream product

• 106-38-7 para-bromotoluene 
• 99-94-5 p-Toluic acid 

Relevant academic research and scientific papers

Rhodium-Catalyzed [2+1+2+1] Cycloaddition of Benzoic Acids with Diynes through Decarboxylation and C≡C Triple Bond Cleavage

It has been established that an electron-deficient cyclopentadienyl rhodium(III) (CpERhIII) complex catalyzes the oxidative and decarboxylative [2+1+2+1] cycloaddition of benzoic acids with diynes through C≡C triple bond cleavage, leading to fused naphthalenes. This cyclotrimerization is initiated by directed ortho C?H bond cleavage of a benzoic acid, and the subsequent regioselective alkyne insertion and decarboxylation produce a five-membered rhodacycle. The electron-deficient nature of the CpERhIII complex promotes reductive elimination giving a cyclobutadiene–rhodium(I) complex rather than the second intermolecular alkyne insertion. The oxidative addition of the thus generated cyclobutadiene to rhodium(I) (formal C≡C triple bond cleavage) followed by the second intramolecular alkyne insertion and reductive elimination give the corresponding [2+1+2+1] cycloaddition product. The synthetic utility of the present [2+1+2+1] cycloaddition was demonstrated in the facile synthesis of a donor–acceptor [5]helicene and a hemi-hexabenzocoronene by a combination with the chemoselective Scholl reaction.

A convenient domino synthesis of 4,9-diphenyl-2,3-dihydro-1H-benzo[f] isoindole derivatives

The first examples are described of a convenient domino synthesis of 4,9-diphenyl-2,3-dihydro-1H-benzo[f]isoindole derivatives in a single operation by means of palladium-catalyzed cyclization of simple 1,6-diynes with aryl halides. Georg Thieme Verlag Stuttgart.