Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction

Progress in Petasis Reaction

“…对 Petasis 反应的机理存在两种 假设 [8] : Petasis 认为, 该反应首先由 α-羟基醛 1 与胺 2 反 应形成中间体 4, 该中间体的羟基与有机硼的空轨道配 位形成的中间体 6 进行分子内亲核进攻水解后得到产物 氨基醇 7 (Path 1, Scheme 1) [1] ; 而 Schlienger 等 [13] 则认为 …”

An improved procedure for the synthesis of arylboronates by palladium‐catalyzed coupling reaction of aryl halides and bis(pinacolato)diboron in polyethylene glycol

“…The solvent was removed in vacuo, and the crude reaction mixture was purified by chromatography on silica gel (hexane-ethyl acetate). 4,5,3, Catalyst, NaOAc [19] ). Anal.…”

“…Aryl boronic acids and their esters are important synthetic targets because they have been extensively applied as precursors in organic reactions, [1] such as the Suzuki-Miyaura reaction, [2] additions to carbonyl compounds, imines and nitriles, [3] heteroatom couplings [4] and multicomponent Petasis-borono Mannich reactions, [5] to construct new carbon-carbon, carbon-nitrogen, carbon-phosphine and carbon-oxygen bonds. In addition, the synthesis of arylboronic esters is a current topic of research in molecular recognition and pharmaceutical development owing to their low toxicity and stability in air and water.…”

Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts

“…Recently, metal-free transformations involving organotrifluoroborates have emerged as an alternative to metal-catalyzed protocols [11]. More specifically, their Lewis acid-catalyzed reactions with stabilized carbocations such as iminium [12] and oxocarbenium ions [13][14][15][16] have been explored. However, the drawbacks to these methods are that they rely on the generation of unstable boron dihalide species thereby resulting in low functional group tolerance.…”