Hydroboration with pyridine borane at room temperature.
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.
Clay
Julia M
JM
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Vedejs
Edwin
E
D000438:Alcohols / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry*; D013696:Temperature
D000438:Alcohols; D000475:Alkenes; D000480:Alkynes; D001896:Boron Compounds; D007659:Ketones; D011725:Pyridines; C041928:pyridine borane