Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics

Tahir N. Majid; Ming Chang P. Yeh; Paul Knochel

doi:10.1016/S0040-4039(01)93449-5

Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics

Tahir N. Majid^*, Ming Chang P. Yeh, Paul Knochel

^*Corresponding author for this work

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

31 Citations (Scopus)

Abstract

Various open-chain and cyclic β-cyano zinc and copper organometallics can be prepared by the reaction of the corresponding organic halides with zinc and subsequent transmetalation with CuCN · 2 LiCl. They react in fair to good yields with various organic electrophiles (enones, allylic bromides and benzoyl chloride) affording highly functionalized nitriles. High diastereoselectivities have been observed in coupling reactions with the cyclic 2-cyano organocopper derivatives. The x-ray structure of cyanoethylzinc iodide is also reported.

Original language	English
Pages (from-to)	5069-5072
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(01)93449-5
Publication status	Published - 1989
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics",

abstract = "Various open-chain and cyclic β-cyano zinc and copper organometallics can be prepared by the reaction of the corresponding organic halides with zinc and subsequent transmetalation with CuCN · 2 LiCl. They react in fair to good yields with various organic electrophiles (enones, allylic bromides and benzoyl chloride) affording highly functionalized nitriles. High diastereoselectivities have been observed in coupling reactions with the cyclic 2-cyano organocopper derivatives. The x-ray structure of cyanoethylzinc iodide is also reported.",

author = "Majid, {Tahir N.} and Yeh, {Ming Chang P.} and Paul Knochel",

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journal = "Tetrahedron Letters",

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T1 - Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics

AU - Majid, Tahir N.

AU - Yeh, Ming Chang P.

AU - Knochel, Paul

PY - 1989

Y1 - 1989

N2 - Various open-chain and cyclic β-cyano zinc and copper organometallics can be prepared by the reaction of the corresponding organic halides with zinc and subsequent transmetalation with CuCN · 2 LiCl. They react in fair to good yields with various organic electrophiles (enones, allylic bromides and benzoyl chloride) affording highly functionalized nitriles. High diastereoselectivities have been observed in coupling reactions with the cyclic 2-cyano organocopper derivatives. The x-ray structure of cyanoethylzinc iodide is also reported.

AB - Various open-chain and cyclic β-cyano zinc and copper organometallics can be prepared by the reaction of the corresponding organic halides with zinc and subsequent transmetalation with CuCN · 2 LiCl. They react in fair to good yields with various organic electrophiles (enones, allylic bromides and benzoyl chloride) affording highly functionalized nitriles. High diastereoselectivities have been observed in coupling reactions with the cyclic 2-cyano organocopper derivatives. The x-ray structure of cyanoethylzinc iodide is also reported.

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VL - 30

SP - 5069

EP - 5072

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics

Abstract

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