Synthesis of pinacol esters of 2,3-alkadienylboronic acid via the copper(I) mediated coupling reaction of Knochel's (dialkoxyboryl)methylzinc reagents with propargylic tosylates

Ilya Gridnev, Gen Kanai, Norio Miyaura, Akira Suzuki

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The reaction of propargyl tosylates (1) with (dialkoxyboryl)methyl-copper(I) reagents, prepared in situ from Knochel's (dialkoxyboryl)-methylzinc iodide (2) and CuCN · 2LiCl, produced 2,3-alkadienyl-boronates (3) in moderate yields. The reaction proceeded regioselectively to provide an SN2' substitution product without contamination by other products such as 3-alkynylboronate.

Original languageEnglish
Pages (from-to)C4-C7
JournalJournal of Organometallic Chemistry
Volume481
Issue number1
DOIs
Publication statusPublished - 1994 Nov 1
Externally publishedYes

Keywords

  • Boron
  • Boronic acid
  • Copper
  • Coupling reaction
  • Palladium
  • Zinc

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Fingerprint Dive into the research topics of 'Synthesis of pinacol esters of 2,3-alkadienylboronic acid via the copper(I) mediated coupling reaction of Knochel's (dialkoxyboryl)methylzinc reagents with propargylic tosylates'. Together they form a unique fingerprint.

Cite this