Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
J Org Chem. 2014 Jan 3;79(1):365-78. doi: 10.1021/jo402616w. Epub 2013 Dec 11.
Azaborines are an important class of compounds with applications in both medicinal chemistry and materials science. The first borazaronaphthalene, 2-chloro-2,1-borazaronaphthalene, was reported in 1959; however, access to more highly functionalized substructures has been limited because of the harsh reaction conditions required to displace the chloride on boron. A convergent approach has been developed to synthesize disubstituted 2,1-borazaronaphthalenes from N-substituted 2-aminostyrenes and potassium organotrifluoroborates, where the potassium organotrifluoroborate is converted to the active R-BX2 species (X = Cl or F) in situ by addition of a fluorophile. Starting from aryl-, heteroaryl-, alkynyl-, alkenyl-, and alkyltrifluoroborates, a library of highly functionalized 2,1-borazaronaphthalenes were synthesized in one step under mild, transition-metal-free conditions.
氮硼杂环化合物是一类重要的化合物，在药物化学和材料科学领域都有应用。第一个苯并硼杂萘，2-氯-2,1-苯并硼杂萘，于 1959 年报道；然而，由于取代硼上的氯需要苛刻的反应条件，因此更高度官能化的亚结构的获得受到限制。已经开发出一种从 N-取代的 2-氨基苯乙烯和有机钾三氟硼酸盐合成二取代 2,1-苯并硼杂萘的汇聚方法，其中通过添加亲氟试剂，有机钾三氟硼酸盐原位转化为活性 R-BX2 物种（X = Cl 或 F）。从芳基、杂芳基、炔基、烯基和烷基三氟硼酸盐出发，在温和、无过渡金属的条件下，一步合成了一系列高度官能化的 2,1-苯并硼杂萘。
