Preparation of 2-fluoro-3-aminophenylboronates via directed ortho -metalation

Article abstract of DOI:10.1055/s-0030-1260019

The aromatic amine in fluoroanilines was protected with 2,2,5,5-tetramethyl-1-aza-2,5-disila-cyclopentane (stabase) in order to direct metalation ortho to the fluorine. A series of novel 2-fluoro-3- aminophenylboronates were prepared after quenching the metalated intermediate with triisopropylborate and deprotection in situ. The presented method is convenient and scalable, because all of the synthetic steps use crude intermediates. Several transformations are carried out in the same pot, and the final boronates are easily purified crystalline materials. Georg Thieme Verlag Stuttgart · New York.