Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1, 6-enynes with bis(pinacolato)diboron. Issue 8 (25th May 2017)

• Record Type: Journal Article
• Authors: Hsieh, Jen-Chieh; Hong, Ya-Chun; Yang, Chun-Ming; Mannathan, Subramaniyan; Cheng, Chien-Hong
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 8(2017)
• Page Start: 1615
• Page End: 1619
• Publication Date: 2017-05-25
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00321h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A highly chemo- and stereoselective nickel-catalyzed borylative cyclization of 1, 6-enynes with bis(pinacolato)diboron. Abstract : 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.