Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones

Mirza A. Saputra; Ly Ngo; Rendy Kartika

doi:10.1021/acs.joc.5b01137

Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones

Mirza A. Saputra, Ly Ngo, Rendy Kartika

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23 Citations (Scopus)

Abstract

Herein, we describe a mild method to prepare aliphatic and aromatic vinyl chlorides from their corresponding ketones via triphosgene-pyridine activation in dichloromethane at reflux. The mechanism of this reaction is proposed to involve formation of a putative α-chloro pyridinium carbamate intermediate, which appeared to readily undergo E2 elimination in the presence of pyridine.

Original language	English
Pages (from-to)	8815-8820
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.5b01137
Publication status	Published - 6 Aug 2015

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title = "Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones",

abstract = "Herein, we describe a mild method to prepare aliphatic and aromatic vinyl chlorides from their corresponding ketones via triphosgene-pyridine activation in dichloromethane at reflux. The mechanism of this reaction is proposed to involve formation of a putative α-chloro pyridinium carbamate intermediate, which appeared to readily undergo E2 elimination in the presence of pyridine.",

author = "Saputra, {Mirza A.} and Ly Ngo and Rendy Kartika",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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AU - Saputra, Mirza A.

AU - Ngo, Ly

AU - Kartika, Rendy

PY - 2015/8/6

Y1 - 2015/8/6

N2 - Herein, we describe a mild method to prepare aliphatic and aromatic vinyl chlorides from their corresponding ketones via triphosgene-pyridine activation in dichloromethane at reflux. The mechanism of this reaction is proposed to involve formation of a putative α-chloro pyridinium carbamate intermediate, which appeared to readily undergo E2 elimination in the presence of pyridine.

AB - Herein, we describe a mild method to prepare aliphatic and aromatic vinyl chlorides from their corresponding ketones via triphosgene-pyridine activation in dichloromethane at reflux. The mechanism of this reaction is proposed to involve formation of a putative α-chloro pyridinium carbamate intermediate, which appeared to readily undergo E2 elimination in the presence of pyridine.

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U2 - 10.1021/acs.joc.5b01137

DO - 10.1021/acs.joc.5b01137

M3 - Article

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VL - 80

SP - 8815

EP - 8820

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones

Abstract

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