Clay Julia M, Vedejs Edwin
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
J Am Chem Soc. 2005 Apr 27;127(16):5766-7. doi: 10.1021/ja043743j.
Treatment of pyridine borane (Py.BH3) with iodine, bromine, or strong acids affords activated Py.BH2X complexes that are capable of hydroborating alkenes at room temperature. Evidence is presented for an unusual hydroboration mechanism involving leaving group displacement. In contrast to THF.BH3, hydroboration with Py.BH2I selectively affords the monoadducts. The crude hydroboration products are converted into synthetically useful potassium alkyltrifluoroborate salts upon treatment with methanolic KHF2.
用碘、溴或强酸处理吡啶硼烷(Py.BH₃)可得到活化的Py.BH₂X配合物,这些配合物能够在室温下对烯烃进行硼氢化反应。本文提供了涉及离去基团取代的异常硼氢化反应机理的证据。与THF.BH₃不同,用Py.BH₂I进行硼氢化反应可选择性地得到单加合物。粗硼氢化产物在用甲醇KHF₂处理后可转化为具有合成用途的烷基三氟硼酸钾盐。