S(n)AR reactions with fluoroarene-Cr(CO)2L complexes, where L is a potential linker ligand for solid phase synthesis

M. F. Semmelhack; Gerhard Hilt; Jeremy H. Colley

doi:10.1016/S0040-4039(98)01720-1

S(n)AR reactions with fluoroarene-Cr(CO)₂L complexes, where L is a potential linker ligand for solid phase synthesis

M. F. Semmelhack, Gerhard Hilt, Jeremy H. Colley

Chemistry

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

28 Scopus citations

Abstract

Fluoroarene-Cr(CO)₂L complexes with L = CO, PPh₃, P(OPh)₃, P(pyrrolyl)₃, and P(pyrrolyl)₂(NMeBn) have been evaluated for rates of nucleophilic substitution by amines and other nucleophiles. While there is a strong effect on relative rates depending on nucleophile type and the electronic effects of L, the P(pyrrolyl)₃ and P(pyrrolyl)₂-(NMeBn) complexes show general reactivity comparable to the parent complexes, with L = CO.

Original language	English (US)
Pages (from-to)	7683-7686
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	42
DOIs	https://doi.org/10.1016/S0040-4039(98)01720-1
State	Published - Oct 15 1998

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Fluoroarene-chromium
Nucleophilic substitution
P(pyrrolyl)
S(N)Ar

Access to Document

10.1016/S0040-4039(98)01720-1

Cite this

@article{0e0145989db7431689d0b035ef8ab5f1,

title = "S(n)AR reactions with fluoroarene-Cr(CO)2L complexes, where L is a potential linker ligand for solid phase synthesis",

abstract = "Fluoroarene-Cr(CO)2L complexes with L = CO, PPh3, P(OPh)3, P(pyrrolyl)3, and P(pyrrolyl)2(NMeBn) have been evaluated for rates of nucleophilic substitution by amines and other nucleophiles. While there is a strong effect on relative rates depending on nucleophile type and the electronic effects of L, the P(pyrrolyl)3 and P(pyrrolyl)2-(NMeBn) complexes show general reactivity comparable to the parent complexes, with L = CO.",

keywords = "Fluoroarene-chromium, Nucleophilic substitution, P(pyrrolyl), S(N)Ar",

author = "Semmelhack, {M. F.} and Gerhard Hilt and Colley, {Jeremy H.}",

year = "1998",

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doi = "10.1016/S0040-4039(98)01720-1",

language = "English (US)",

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T1 - S(n)AR reactions with fluoroarene-Cr(CO)2L complexes, where L is a potential linker ligand for solid phase synthesis

AU - Semmelhack, M. F.

AU - Hilt, Gerhard

AU - Colley, Jeremy H.

PY - 1998/10/15

Y1 - 1998/10/15

N2 - Fluoroarene-Cr(CO)2L complexes with L = CO, PPh3, P(OPh)3, P(pyrrolyl)3, and P(pyrrolyl)2(NMeBn) have been evaluated for rates of nucleophilic substitution by amines and other nucleophiles. While there is a strong effect on relative rates depending on nucleophile type and the electronic effects of L, the P(pyrrolyl)3 and P(pyrrolyl)2-(NMeBn) complexes show general reactivity comparable to the parent complexes, with L = CO.

AB - Fluoroarene-Cr(CO)2L complexes with L = CO, PPh3, P(OPh)3, P(pyrrolyl)3, and P(pyrrolyl)2(NMeBn) have been evaluated for rates of nucleophilic substitution by amines and other nucleophiles. While there is a strong effect on relative rates depending on nucleophile type and the electronic effects of L, the P(pyrrolyl)3 and P(pyrrolyl)2-(NMeBn) complexes show general reactivity comparable to the parent complexes, with L = CO.

KW - Fluoroarene-chromium

KW - Nucleophilic substitution

KW - P(pyrrolyl)

KW - S(N)Ar

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