Direct C–H borylation of vinylporphyrins via copper catalysis

Abstract

A method of direct borylation of vinyl-substituted porphyrinoids (porphyrins and chlorins) has been developed based on the copper catalyzed vinylic C-H activation. Ni(II) complexes of meso- and β-vinylporphyrinoids have been...

Biaryl carboxamide‐based peptidomimetics analogs as potential pancreatic lipase inhibitors for treating obesity

“…[34] The halogenated aromatic carboxylic acid was reacted with a substituted boronic acid in the presence of potassium phosphate tribasic (K 3 PO 4 ), tetrakis(triphenylphosphine)palladium(0) (Pd(Ph3) 4 ) in N,N-dimethylformamide (DMF), at 105°C under a nitrogen atmosphere for 20 h to give 1,1′-biphenyl-3-carboxylic acid (1-2). [35] Further, substituted 1,1′biphenyl-3-carboxylic acids were reacted with methyl L-leucinate in the presence of coupling reagents hydroxybenzotriazole(HOBt), N-(3dimethylamino-propyl)-N'-ethylcarbodiimide hydrochloride (EDC.HCl), and N,N-diisopropylethylamine in dry DMF to give substituted methyl 1,1′-biphenyl-4-carbonyl-L-leucinate (3)(4). [36] The synthesized substituted methyl 1,1′-biphenyl-4-carbonyl-L-leucinate was stirred in methanol in the presence of sodium hydroxide at 50°C to give substituted 1,1′-biphenyl-4-carbonyl-L-leucine carboxylic acid (5)(6).…”

Meso-Formyl, Vinyl, and Ethynyl Porphyrins—Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

“…The meso-vinyl group can also be functionalized via catalytic direct CH-functionalization reactions. The direct C-H borylation of the meso-vinyl group in NiOEP 54 was performed with Cu(II) complex as a catalyst, yielding the meso-(2-pinacolboronylethenyl)porphyrin 103Ni, which was shown to act as a nucleophilic partner in the Suzuki cross-coupling leading to porphyrin derivatives 104 and 105 with an extended π-conjugation through the carbon double bond [85]. The oxidative homocoupling of the borylporphyrin 103Pd produced the dimer 106 (Scheme 41) [86].…”

“…through the carbon double bond [85]. The oxidative homocoupling of the borylporphyrin 103Pd produced the dimer 106 (Scheme 41) [86].…”

Syntheses, characterizations and catalytic properties of three zinc complexes and one lithium compound chelated by β-diketiminate ligands

“…36,37 However, the reactions required noble metal catalysts, including Ir, 38,39 Rh, 40 and Pt. 41 Recently, Cu 42,43 and Zn 44,45 have been recognized as efficient surrogates of these noble metal catalysts. However, there are very few such compounds.…”