A general method of halogenation for synthesis of α-halodifluoromethyl ketones and [18F]-labeled trifluoromethyl ketones

G. K.Surya Prakash; Jinbo Hu; Mian M. Alauddin; Peter S. Conti; George A. Olah

doi:10.1016/S0022-1139(03)00039-3

A general method of halogenation for synthesis of α-halodifluoromethyl ketones and [¹⁸F]-labeled trifluoromethyl ketones

G. K.Surya Prakash, Jinbo Hu, Mian M. Alauddin, Peter S. Conti, George A. Olah

Cancer Systems Imaging

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

23 Scopus citations

Abstract

A convenient general method of halogenations suitable for synthesis of α-halodifluoromethyl ketones is reported. Reaction of 2,2-difluoro-1-aryl-1-trimethylsiloxyethenes (difluoro silyl enol ethers) (2a-e) with halogens at low temperature (-30 to -78 °C) produced a high yield of α-halodifluoromethyl ketones (1a-j). This one-step simple method can be highly useful for synthesis of [¹⁸F]-labeled α-trifluoromethyl ketones.

Original language	English (US)
Pages (from-to)	239-243
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	121
Issue number	2
DOIs	https://doi.org/10.1016/S0022-1139(03)00039-3
State	Published - Jun 1 2003

Keywords

Electrophilic fluorination
Fluorine-18
Halogenation

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/S0022-1139(03)00039-3

Cite this

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title = "A general method of halogenation for synthesis of α-halodifluoromethyl ketones and [18F]-labeled trifluoromethyl ketones",

abstract = "A convenient general method of halogenations suitable for synthesis of α-halodifluoromethyl ketones is reported. Reaction of 2,2-difluoro-1-aryl-1-trimethylsiloxyethenes (difluoro silyl enol ethers) (2a-e) with halogens at low temperature (-30 to -78 °C) produced a high yield of α-halodifluoromethyl ketones (1a-j). This one-step simple method can be highly useful for synthesis of [18F]-labeled α-trifluoromethyl ketones.",

keywords = "Electrophilic fluorination, Fluorine-18, Halogenation",

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T1 - A general method of halogenation for synthesis of α-halodifluoromethyl ketones and [18F]-labeled trifluoromethyl ketones

AU - Prakash, G. K.Surya

AU - Hu, Jinbo

AU - Alauddin, Mian M.

AU - Conti, Peter S.

AU - Olah, George A.

PY - 2003/6/1

Y1 - 2003/6/1

N2 - A convenient general method of halogenations suitable for synthesis of α-halodifluoromethyl ketones is reported. Reaction of 2,2-difluoro-1-aryl-1-trimethylsiloxyethenes (difluoro silyl enol ethers) (2a-e) with halogens at low temperature (-30 to -78 °C) produced a high yield of α-halodifluoromethyl ketones (1a-j). This one-step simple method can be highly useful for synthesis of [18F]-labeled α-trifluoromethyl ketones.

AB - A convenient general method of halogenations suitable for synthesis of α-halodifluoromethyl ketones is reported. Reaction of 2,2-difluoro-1-aryl-1-trimethylsiloxyethenes (difluoro silyl enol ethers) (2a-e) with halogens at low temperature (-30 to -78 °C) produced a high yield of α-halodifluoromethyl ketones (1a-j). This one-step simple method can be highly useful for synthesis of [18F]-labeled α-trifluoromethyl ketones.

KW - Electrophilic fluorination

KW - Fluorine-18

KW - Halogenation

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