Benzoxaboroles are cyclic derivatives of boronic acids that have recently gained the attention of both the pharmaceutical industry and the synthetic community. Because benzoxaboroles are more hydrolytically stable than the corresponding boronic acids, there is currently a dearth of benzoxaborole protecting groups. However, as more complex benzoxaboroles are synthesized, chemical incompatibility is inevitable. This paper describes a robust, inexpensive method of protection of benzoxaboroles using three protecting groups. One group is an easily cleavable protecting group for one-step reactions while the other two have proven to increase the stability of benzoxaboroles to numerous reaction conditions and are suitable for multi-step synthesis. Additionally, these groups are readily deprotected under mild aquous acid conditions and allow for chromatography-free re-isolation of the benzoxaborole in good yields.

Protection of the benzoxaborole functionality: Synthesis and functionalization of zwitterionic benzoxaborole complexes

255th National Meeting (2018)

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