Reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with N-halogeno compound in THF–DMF: a novel synthesis of 1,2-disubstituted (E)-vinyl bromides

✍ Scribed by Masayuki; Kazuya Shirakawa

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 158 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00213-6

✦ Synopsis

DMF-induced reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with an N-halogeno compound results in 1,2migration of an alkyl group from the dialkylboryl group to the α-carbon atom without elimination of the bromine atom, followed by β-elimination to provide 1,2-disubstituted (E)-vinyl bromides stereoselectively in good yields.