SYNTHESIS OF PINACOL ESTERS OF 2,3-ALKADIENYLBORONIC ACID VIA THE COPPER(I) MEDIATED COUPLING REACTION OF KNOCHELS (DIALKOXYBORYL) METHYLZINC REAGENTS WITH PROPARGYLIC TOSYLATES

Authors
GRIDNEV I KANAI G MIYAURA N SUZUKI A
Citation
I. Gridnev et al., SYNTHESIS OF PINACOL ESTERS OF 2,3-ALKADIENYLBORONIC ACID VIA THE COPPER(I) MEDIATED COUPLING REACTION OF KNOCHELS (DIALKOXYBORYL) METHYLZINC REAGENTS WITH PROPARGYLIC TOSYLATES, Journal of organometallic chemistry, 481(1), 1994, pp. 30000004-30000007
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of organometallic chemistry → ACNP
ISSN journal
0022328X
Volume
481
Issue
1
Year of publication
1994
Pages
30000004 - 30000007
Database
ISI
SICI code
0022-328X(1994)481:1<30000004:SOPEO2>2.0.ZU;2-X
Abstract
The reaction of propargyl tosylates (1) with (dialkoxyboryl)methyl-cop per(I) reagents, prepared in situ from Knochel's (dialkoxyboryl)-methy lzinc iodide (2) and CuCN.2LiCl, produced 2,3-alkadienyl-boronates (3) in moderate yields. The reaction proceeded regioselectively to provid e an S(N)2' substitution product without contamination by other produc ts such as 3-alkynylboronate.