School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan.
Org Biomol Chem. 2013 Dec 14;11(46):8145-50. doi: 10.1039/c3ob41787e.
Nucleophilic addition of amines to 3-[(dan)boryl]benzynes (dan = 1,8-diaminonaphthalene) generated by a fluoride ion proceeded with high ortho-selectivity to give 2-borylaniline derivatives, under conditions that are tolerant to various functional groups. The (dan)boryl group of the adduct was hydrolyzed into a boronic acid under acidic conditions, which could further serve for various C-C, C-O, C-N, and C-H bond-formation reactions. The overall process provides a promising entry for preparing multisubstituted aniline derivatives.
伯胺的亲核加成反应到 3-[(dan)硼基]苯乙炔（dan = 1,8-二氨基萘）通过氟离子进行，在对各种官能团具有耐受性的条件下，以高邻位选择性得到 2-硼酰苯胺衍生物。加合物中的(dan)硼基在酸性条件下水解成硼酸，硼酸可以进一步用于各种 C-C、C-O、C-N 和 C-H 键形成反应。整个过程为制备多取代苯胺衍生物提供了一个很有前途的途径。
