Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C{double bond, long}N double bonds

Fabien Cougnon; Laurence Feray; Samantha Bazin; Michèle P. Bertrand

doi:10.1016/j.tet.2007.09.014

Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C{double bond, long}N double bonds

Fabien Cougnon, Laurence Feray, Samantha Bazin, Michèle P. Bertrand

Aix-Marseille Université

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

26 Citations (Scopus)

Abstract

Diethylzinc-mediated radical addition to C{double bond, long}N bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of diethylzinc by dimethylzinc, offers no advantage in these reactions.

Original language	English
Pages (from-to)	11959-11964
Number of pages	6
Journal	Tetrahedron
Volume	63
Issue number	48
DOIs	https://doi.org/10.1016/j.tet.2007.09.014
Publication status	Published - 26 Nov 2007
Externally published	Yes

Keywords

Alkyl phenyl telluride
Diethylzinc
Dimethylzinc
Radical addition to imino group

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10.1016/j.tet.2007.09.014

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title = "Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C\{double bond, long\}N double bonds",

abstract = "Diethylzinc-mediated radical addition to C\{double bond, long\}N bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of diethylzinc by dimethylzinc, offers no advantage in these reactions.",

keywords = "Alkyl phenyl telluride, Diethylzinc, Dimethylzinc, Radical addition to imino group",

author = "Fabien Cougnon and Laurence Feray and Samantha Bazin and Bertrand, \{Mich{\`e}le P.\}",

year = "2007",

month = nov,

day = "26",

doi = "10.1016/j.tet.2007.09.014",

language = "English",

volume = "63",

pages = "11959--11964",

journal = "Tetrahedron",

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number = "48",

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TY - JOUR

T1 - Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C{double bond, long}N double bonds

AU - Cougnon, Fabien

AU - Feray, Laurence

AU - Bazin, Samantha

AU - Bertrand, Michèle P.

PY - 2007/11/26

Y1 - 2007/11/26

N2 - Diethylzinc-mediated radical addition to C{double bond, long}N bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of diethylzinc by dimethylzinc, offers no advantage in these reactions.

AB - Diethylzinc-mediated radical addition to C{double bond, long}N bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of diethylzinc by dimethylzinc, offers no advantage in these reactions.

KW - Alkyl phenyl telluride

KW - Diethylzinc

KW - Dimethylzinc

KW - Radical addition to imino group

UR - https://www.scopus.com/pages/publications/35349003378

U2 - 10.1016/j.tet.2007.09.014

DO - 10.1016/j.tet.2007.09.014

M3 - Article

SN - 0040-4020

VL - 63

SP - 11959

EP - 11964

JO - Tetrahedron

JF - Tetrahedron

IS - 48

ER -

Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C{double bond, long}N double bonds

Abstract

Keywords

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