Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron

作者：Hsieh Jen Chieh^*; Hong Ya Chun; Yang Chun Ming; Mannathan Subramaniyan; Cheng Chien Hong^*

来源：Organic Chemistry Frontiers, 2017, 4(8): 1615-1619.

DOI：10.1039/c7qo00321h

A highly chemo- and stereoselective nickel-catalyzed borylative cyclization of 1,6-enynes with bis(pinacolato)diboron is described. Enynes containing an electron-deficient alkene such as a vinyl ketone provided alkenylboronates while enynes containing a terminal alkene gave homoallylic boronates. A plausible mechanism involving a nickelacyclopentene intermediate is proposed. In addition, the resulted alkenyl-or homoallylic boronates can be transformed to the corresponding ketones and alcohols via oxidation. Application to a palladium-catalyzed cross coupling reaction of alkenylboronates with aromatic halides has been demonstrated as well.

• 出版日期2017-8-1
• 单位清华大学