16419-60-6Relevant articles and documents
Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates
Yuen, Alexander K.L.,Hutton, Craig A.
, p. 7899 - 7903 (2005)
An efficient two-step procedure for the deprotection of pinacolyl organoboronate esters is described. Reaction with excess potassium hydrogen fluoride produces the corresponding stable, crystalline potassium organotrifluoroborate salts. Treatment of the trifluoroborates with either inorganic base or trimethylsilyl chloride and water affords the corresponding organoboronic acid in high yield.
Aryllead triacetates in the synthesis of oxaphenanthrene derivatives
Fedorov, Alexey Yu,Carrara, Fabien,Finet, Jean-Pierre
, p. 5875 - 5877 (2001)
Ortho-Halomethylphenyllead triacetates (halo = bromine or chlorine) react with phenols in the presence of triethylamine and a pyridine derivative to afford modest to good yields of dibenzo[b,d]-6H-pyrans.
Method for synthesizing sodium 2-carboxyphenylborate
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Paragraph 0020-0021, (2020/06/17)
The invention discloses a method for synthesizing sodium 2-carboxyphenylborate. The method comprises the following two steps of: 1) taking methyl 2-bromobenzoate as an initial raw material, through bromine removal by butyl lithium, carrying out a one-pot reaction with triisopropyl borate or trimethyl borate to obtain a product 2-methoxycarbonyl phenylboronic acid, and 2) hydrolyzing the 2-methoxycarbonyl phenylboronic acid in a sodium hydroxide methanol solution, and pulping with acetone to obtain sodium 2-carboxyphenylborate monohydrate. The method has the advantages of easily available raw materials, simple operation, safety, environmental protection, low cost and high yield.
Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water
Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg
, p. 1842 - 1851 (2018/02/23)
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
Chen, Kai,Zhang, Shuai,He, Pei,Li, Pengfei
, p. 3676 - 3680 (2016/06/09)
A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.