The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions

Cheng Ming Chu, Wan Ju Huang, Chaowei Lu, Pohsi Wu, Ju Tsung Liu, Ching Fa Yao

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

The 1,4-addition of various thiols to α,β-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with α,β-unsaturated ketones present in the reaction.

Original languageEnglish
Pages (from-to)7375-7380
Number of pages6
JournalTetrahedron Letters
Volume47
Issue number41
DOIs
Publication statusPublished - 2006 Oct 9

Fingerprint

ferrous sulfate
Ketones
Sulfhydryl Compounds
Chlorides
Esters
Iron
Atmosphere
Salts
Air
Catalysts
Temperature

Keywords

  • 1,4-Addition
  • Anhydrous iron(III) chloride
  • Solvent free
  • α,β-Unsaturated ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions. / Chu, Cheng Ming; Huang, Wan Ju; Lu, Chaowei; Wu, Pohsi; Liu, Ju Tsung; Yao, Ching Fa.

In: Tetrahedron Letters, Vol. 47, No. 41, 09.10.2006, p. 7375-7380.

Research output: Contribution to journalArticle

Chu, Cheng Ming ; Huang, Wan Ju ; Lu, Chaowei ; Wu, Pohsi ; Liu, Ju Tsung ; Yao, Ching Fa. / The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 41. pp. 7375-7380.
@article{a3779122f3704e30a3a782756f499276,
title = "The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions",
abstract = "The 1,4-addition of various thiols to α,β-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol {\%}) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with α,β-unsaturated ketones present in the reaction.",
keywords = "1,4-Addition, Anhydrous iron(III) chloride, Solvent free, α,β-Unsaturated ketones",
author = "Chu, {Cheng Ming} and Huang, {Wan Ju} and Chaowei Lu and Pohsi Wu and Liu, {Ju Tsung} and Yao, {Ching Fa}",
year = "2006",
month = "10",
day = "9",
doi = "10.1016/j.tetlet.2006.07.151",
language = "English",
volume = "47",
pages = "7375--7380",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "41",

}

TY - JOUR

T1 - The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions

AU - Chu, Cheng Ming

AU - Huang, Wan Ju

AU - Lu, Chaowei

AU - Wu, Pohsi

AU - Liu, Ju Tsung

AU - Yao, Ching Fa

PY - 2006/10/9

Y1 - 2006/10/9

N2 - The 1,4-addition of various thiols to α,β-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with α,β-unsaturated ketones present in the reaction.

AB - The 1,4-addition of various thiols to α,β-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with α,β-unsaturated ketones present in the reaction.

KW - 1,4-Addition

KW - Anhydrous iron(III) chloride

KW - Solvent free

KW - α,β-Unsaturated ketones

UR - http://www.scopus.com/inward/record.url?scp=33748310881&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748310881&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.07.151

DO - 10.1016/j.tetlet.2006.07.151

M3 - Article

AN - SCOPUS:33748310881

VL - 47

SP - 7375

EP - 7380

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -