Oxidative coupling of 2-methyl furoate: A scalable synthesis of dimethyl 2,2'-bifuran-5,5'-dicarboxylate

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part A: the C(sp2)−C(sp2), C(sp2)−C(sp3) and C(sp3)−C(sp3) Bonds

“…At 90 °C under oxygen pressure and Pd(OAc) 2 catalysis and sodium carboxylates, the homocou-pling of 2-methyl furoate arose in low yields, t-BuCO 2 Na being slightly bette than AcONa and CF 3 CO 2 Na (Scheme 13g). [82] While Murakami, Itami and co-workers proposed that the homocoupling of Scheme 13f occurs via addition of in-situ formed 4-(tert-butyl)pyridin-2-ylpalladium carboxylate with another molecule of 4-(tert-butyl)pyridine, [81] Lobo's team assumed a transmetalation between two Pd II -furoate intermediates (Scheme 13h) for the homocoupling of Scheme 13g, [82] a pathway previously proposed by Stahl's team for the Pd-catalyzed aerobic oxidative coupling of arenes. [83] The oxidative cross-coupling between two partners with similar structures and electronic charac-teristics in avoiding homo-couplings was disclosed using catalytic Pd(OAc) 2 , Ag 2 O and RCO 2 H in DMSO (Scheme 13i).…”

Nickel‐Electrocatalyzed Synthesis of Bifuran‐Based Monomers

“…A typical strategy involves using Pd-catalysis in either BrÀ Br homocoupling, [30][31][32][33][34] Mizoroki-Heck, [28,35] or direct CÀ Hfunctionalization. [36,37] Other approaches include oxidative homocoupling of Grignard reagents [38] and nickel-catalyzed homocoupling of ethyl 5-bromofuroate. [36] Some common hindrances in these protocols are the use of expensive palladium catalysts, [28,[30][31][32][33][34][35][36][37] poisonous CO, [34,39] or metal powders [33,36] as reductants.…”

Comparison of 4,4′-Dimethylbiphenyl from Biomass-Derived Furfural and Oil-Based Resource: Technoeconomic Analysis and Life-Cycle Assessment

“…Thus, the potential market size of the performance-enhanced polyester using monomers from DMBP is significant. On the other hand, using biomass feedstock for chemical production has been established as a promising strategy to alleviate global warming. − It is noteworthy that polyesters could be chemically recycled or upcycled, , further reducing the overall life-cycle emission of using biomass-derived DMBP. With the increased awareness of customers to choose more environmentally friendly products, the market of sustainable DMBP from renewable sources is expected to expand.…”