Sodium-metal-promoted reductive 1,2-syn-diboration of alkynes with reduction-resistant trimethoxyborane

• Ito, Shiori

  Department of Chemistry, Graduate School of Science, Kyoto University

• Fukazawa, Mizuki

  Department of Chemistry, Graduate School of Science, Kyoto University

• Takahashi, Fumiya

  Department of Chemistry, Graduate School of Science, Kyoto University

• Nogi, Keisuke

  Department of Chemistry, Graduate School of Science, Kyoto University

• Yorimitsu, Hideki

  Department of Chemistry, Graduate School of Science, Kyoto University

Bibliographic Information

Other Title

• Sodium-Metal-Promoted Reductive 1,2-<i>syn</i>-Diboration of Alkynes with Reduction-Resistant Trimethoxyborane

Abstract

Reductive 1, 2-diboration of alkynes has been accomplished by means of sodium dispersion in the presence of trimethoxyborane as a reduction-resistant boron electrophile. Two boron moieties can be introduced onto alkynes with excellent syn selectivity to afford the corresponding (Z)-1, 2-diborylalkenes. Bis(borate) species generated in situ can be involved in one-pot Suzuki-Miyaura arylation, formal arylboration of alkynes thus being executed.

Journal

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 93 (10), 1171-1179, 2020-10

  Chemical Society of Japan

Keywords

• 1, 2-Diboration
• Alkyne
• Sodium metal

Details

• CRID: 1051130853452589824
• NII Article ID: 130007926134
• ISSN: 00092673
• ISSN: 13480634
• DOI: 10.1246/bcsj.20200110
• HANDLE: 2433/255899
• Web Site: https://academic.oup.com/bcsj/article-pdf/93/10/1171/56305215/bcsj.20200110.pdf
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN