214907-25-2Relevant academic research and scientific papers
Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates
Liu, Shiwen,Meng, Lingling,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo
, p. 913 - 917 (2021/04/05)
Main observation and conclusion: We have developed an efficient synthesis of acrylonitriles via mild base promoted tandem nucleophilic substitution-isomerization of α-cyanohydrin methanesulfonates with alkenylboronic acids. This transition metal-free protocol works under simple and mild conditions and offers good chemical yields for a wide range of substrates and demonstrates good functional group tolerance. (Figure presented.).
Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates
Corless, Victoria B.,Holownia, Aleksandra,Foy, Hayden,Mendoza-Sanchez, Rodrigo,Adachi, Shinya,Dudding, Travis,Yudin, Andrei K.
supporting information, p. 5300 - 5303 (2018/09/12)
As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon-metalloid bonds, the synthesis of α-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.
Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles
Lee, C. Frank,Holownia, Aleksandra,Bennett, James M.,Elkins, Jonathan M.,St. Denis, Jeffrey D.,Adachi, Shinya,Yudin, Andrei K.
supporting information, p. 6264 - 6267 (2017/05/19)
Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized.
