An improved procedure for the preparation of aryl- and hetarylacetylenes

Abstract

A number of relatively volatile acetylenes RC ≡ CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC ≡ CC(CH₃)₂OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC ≡ CC(CH₃)₂OH.

Original language	English
Pages (from-to)	589-590
Number of pages	2
Journal	Synthesis
Issue number	5
Publication status	Published - 1 Jan 1996
Externally published	Yes

Keywords

acetylenic alcohols
hetarylacetylenes
KOH-catalyzed elimination of acetone
retro-Favorsky reaction
synthesis of 2-iodo-1-methylpyrrole

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "An improved procedure for the preparation of aryl- and hetarylacetylenes",

abstract = "A number of relatively volatile acetylenes RC ≡ CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC ≡ CC(CH3)2OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC ≡ CC(CH3)2OH.",

keywords = "acetylenic alcohols, hetarylacetylenes, KOH-catalyzed elimination of acetone, retro-Favorsky reaction, synthesis of 2-iodo-1-methylpyrrole",

author = "Mal'Kina, {A. G.} and L. Brandsma and Vasilevsky, {S. F.} and Trofimov, {B. A.}",

year = "1996",

month = jan,

day = "1",

language = "English",

pages = "589--590",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "5",

}

TY - JOUR

T1 - An improved procedure for the preparation of aryl- and hetarylacetylenes

AU - Mal'Kina, A. G.

AU - Brandsma, L.

AU - Vasilevsky, S. F.

AU - Trofimov, B. A.

PY - 1996/1/1

Y1 - 1996/1/1

N2 - A number of relatively volatile acetylenes RC ≡ CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC ≡ CC(CH3)2OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC ≡ CC(CH3)2OH.

AB - A number of relatively volatile acetylenes RC ≡ CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC ≡ CC(CH3)2OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC ≡ CC(CH3)2OH.

KW - acetylenic alcohols

KW - hetarylacetylenes

KW - KOH-catalyzed elimination of acetone

KW - retro-Favorsky reaction

KW - synthesis of 2-iodo-1-methylpyrrole

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M3 - Article

AN - SCOPUS:0029955629

SP - 589

EP - 590

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 5

ER -