Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes

Wenwei Lin; Florian Ilgen; Paul Knochel

doi:10.1016/j.tetlet.2006.01.071

Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes

Wenwei Lin
, Florian Ilgen
, Paul Knochel^*

^*Corresponding author for this work

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

27 Citations (Scopus)

Abstract

The described polyfunctional arylmagnesium reagents, resulting from the highly regioselective addition of magnesium phenylselenide to functionalized arynes, can be trapped by a range of electrophiles, yielding polyfunctional selenoethers in 45-85% yields. Furthermore, these Grignard reagents can be used in Negishi cross-coupling reactions with iodoarenes after transmetalation to the corresponding arylzinc compounds, furnishing functionalized biaryl products in 55-73% yields.

Original language	English
Pages (from-to)	1941-1944
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2006.01.071
Publication status	Published - 2006 Mar 20
Externally published	Yes

Keywords

Aryne
Organomagnesium reagent
Selenoether

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.01.071

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title = "Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes",

abstract = "The described polyfunctional arylmagnesium reagents, resulting from the highly regioselective addition of magnesium phenylselenide to functionalized arynes, can be trapped by a range of electrophiles, yielding polyfunctional selenoethers in 45-85\% yields. Furthermore, these Grignard reagents can be used in Negishi cross-coupling reactions with iodoarenes after transmetalation to the corresponding arylzinc compounds, furnishing functionalized biaryl products in 55-73\% yields.",

keywords = "Aryne, Organomagnesium reagent, Selenoether",

author = "Wenwei Lin and Florian Ilgen and Paul Knochel",

note = "Funding Information: We thank the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG) and Merck Research Laboratories (MSD) for financial support. We also thank Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for the generous gift of chemicals.",

year = "2006",

month = mar,

day = "20",

doi = "10.1016/j.tetlet.2006.01.071",

language = "English",

volume = "47",

pages = "1941--1944",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes

AU - Lin, Wenwei

AU - Ilgen, Florian

AU - Knochel, Paul

N1 - Funding Information: We thank the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG) and Merck Research Laboratories (MSD) for financial support. We also thank Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for the generous gift of chemicals.

PY - 2006/3/20

Y1 - 2006/3/20

N2 - The described polyfunctional arylmagnesium reagents, resulting from the highly regioselective addition of magnesium phenylselenide to functionalized arynes, can be trapped by a range of electrophiles, yielding polyfunctional selenoethers in 45-85% yields. Furthermore, these Grignard reagents can be used in Negishi cross-coupling reactions with iodoarenes after transmetalation to the corresponding arylzinc compounds, furnishing functionalized biaryl products in 55-73% yields.

AB - The described polyfunctional arylmagnesium reagents, resulting from the highly regioselective addition of magnesium phenylselenide to functionalized arynes, can be trapped by a range of electrophiles, yielding polyfunctional selenoethers in 45-85% yields. Furthermore, these Grignard reagents can be used in Negishi cross-coupling reactions with iodoarenes after transmetalation to the corresponding arylzinc compounds, furnishing functionalized biaryl products in 55-73% yields.

KW - Aryne

KW - Organomagnesium reagent

KW - Selenoether

UR - https://www.scopus.com/pages/publications/32644469276

UR - https://www.scopus.com/pages/publications/32644469276#tab=citedBy

U2 - 10.1016/j.tetlet.2006.01.071

DO - 10.1016/j.tetlet.2006.01.071

M3 - Article

AN - SCOPUS:32644469276

SN - 0040-4039

VL - 47

SP - 1941

EP - 1944

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes

Abstract

Keywords

ASJC Scopus subject areas

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