126550-64-9

Upstream product

• 214536-72-8 methyl 4-(5-oxo-1-hexenyl)benzoate 
• 619-44-3 methyl 4-iodobenzoate 
• 98875-45-7 2-(CH₃CO(CH₂)4)-1,3,2-benzodioxaborole 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 109-49-9 5-Hexen-2-one 
• 73166-52-6 4-(3-oxo-1-propen-1-yl)benzoic acid methyl ester 
• 1571-08-0 methyl 4-formylbenzoate 

Relevant academic research and scientific papers

Samarium(II)-promoted radical spirocyclization onto an aromatic ring

Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.

Synthesis of 7-methyl derivatives of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), 5,10-dideaza-5,6,7,8-tetrahydrohomofolic acid (HDDATHF), and LY254155

7-Methyl derivatives of DDATHF, homoDDATHF and the thiophene analog of DDATHF (LY254155) were prepared as potential antitumor agents.

Cross-Coupling Reaction of Alkyl- or Arylboronic Acid Esters with Organic Halides Induced by Thallium(I) Salts and Palladium-Catalyst

The cross-coupling reaction of alkylboronic acid esters with 1-alkenyl- or aryl halides is succesfully catalyzed by PdCl2 (dppf) or Pd(PPh3)4 in the presence of thallium(I) hydroxide or carbonate to give the corresponding alkenes or arenes in good yields.The coupling reaction of arylboronic acid esters with aryl halides under similar conditions to provide biaryls is also described.