1072960-66-7Relevant articles and documents
A Mild Method for Making MIDA Boronates
Kelly, Aidan M.,Chen, Peng-Jui,Klubnick, Jenna,Blair, Daniel J.,Burke, Martin D.
, p. 9408 - 9414 (2020)
We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.
Synthesis of Benzimidazoles bearing borionic acid functionality via metal-free aerobic oxidation
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Paragraph 0226-0028, (2017/02/24)
The present invention relates to benzimidazole derivative useful as a natural product, and as an intermediate product for synthesizing a medicine by having a boronic functional group in a molecule, and to a method to synthesize the benzimidazole derivative in an environment friendly way. More particularly, the present invention relates to a method to manufacture benzimidazole derivative having a boronic functional group in a molecule by using an aerobic oxidation cyclization reaction using air as an oxidizing agent under the presence of an alkaline metal halide or alkali earth metal halide catalyst in an anhydrous condition.COPYRIGHT KIPO 2016
Synthesis of Benzimidazole-Substituted Arylboronic Acids via Aerobic Oxidation of 1,2-Arylenediamines and Formyl-Substituted Aryl MIDA Boronates using Potassium Iodide as a Catalyst
Lee, Ye-Sol,Cheon, Cheol-Hong
supporting information, p. 2951 - 2956 (2015/09/28)
A highly efficient protocol for the synthesis of benzimidazole-substituted arylboronic acids was developed via aerobic oxidative cyclization of 1,2-aryldiamines and formyl-substituted aryl MIDA (N-methyliminodiacetic acid) boronates using potassium iodide as a nucleophilic catalyst. Furthermore, a one-pot protocol for the synthesis of benzimidazole-substituted arylboronic acids from 1,2-phenylenediamines and formyl-substituted arylboronic acids was developed without the isolation of any intermediates. The resulting boronic acids were further subjected to Suzuki-Miyaura coupling reactions without isolation, leading to diaryl-substituted benzimidazoles with only one separation step.
Synthetic Method of Benzimidazole via Aerobic Oxidation
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Paragraph 0214, (2016/11/14)
The present invention relates to a method which naturally synthesizes benzimidazole by reacting aryl diamine and aldehyde through using aerobic oxidative cyclization which uses water or alkali metal halide as a catalyst, and oxygen or oxygen in the air as an oxidizing agent, under DMF or an alcohol solvent.
Multistep synthesis of complex boronic acids from simple MIDA boronates
Gillis, Eric P.,Burke, Martin D.
supporting information; experimental part, p. 14084 - 14085 (2009/03/11)
Due to its sensitivity to most synthetic reagents, it is typically necessary to introduce the boronic acid functional group just prior to its utilization. Overcoming this important limitation, we herein report that air- and chromatographically stable MIDA boronates are compatible with a wide range of common reagents which enables the multistep synthesis of complex boronic acid building blocks from simple B-containing starting materials. X-ray and variable temperature NMR studies link the unique stability of MIDA boronates to a kinetic inaccessibility of the potentially reactive boron p-orbital and/or nitrogen lone pair. These findings were collectively harnessed to achieve a short and modular total synthesis of (+)-crocacin C via the iterative cross-coupling of a structurally complex, MIDA-protected haloboronic acid building block. Copyright
