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

doi:10.1016/0022-328X(94)85018-6

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 journal › Article › peer-review

17 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 S_N2' substitution product without contamination by other products such as 3-alkynylboronate.

Original language	English
Pages (from-to)	C4-C7
Journal	Journal of Organometallic Chemistry
Volume	481
Issue number	1
DOIs	https://doi.org/10.1016/0022-328X(94)85018-6
Publication status	Published - 1994 Nov 1
Externally published	Yes

Keywords

Boron
Boronic acid
Copper
Coupling reaction
Palladium
Zinc

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/0022-328X(94)85018-6

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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. / Gridnev, Ilya; Kanai, Gen; Miyaura, Norio et al.

In: Journal of Organometallic Chemistry, Vol. 481, No. 1, 01.11.1994, p. C4-C7.

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Gridnev, Ilya

AU - Kanai, Gen

AU - Miyaura, Norio

AU - Suzuki, Akira

PY - 1994/11/1

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N2 - 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.

AB - 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.

KW - Boron

KW - Boronic acid

KW - Copper

KW - Coupling reaction

KW - Palladium

KW - Zinc

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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

Abstract

Keywords

ASJC Scopus subject areas

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