Ceric ammonium nitrate (CAN) as a green and highly efficient promoter for the 1,4-addition of thiols and benzeneselenol to α,β-unsaturated ketones

Cheng Ming Chu, Shijay Gao, M. N.V. Sastry, Chun Wei Kuo, Chaowei Lu, Ju Tsung Liu, Ching-Fa Yao

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

A mild and efficient process for the 1,4-addition of thiols and benzeneselenols to various α,β-unsaturated ketones using a catalytic amount of CAN with excellent product yields is described. This inexpensive, nontoxic, and readily available catalytic ceric(IV) ammonium nitrate system efficiently catalyzes conjugate addition reactions between thiol derivatives and various α,β-unsaturated ketones under solvent-free conditions. A plausible mechanism for the role of CAN, both as a promoter in free radical chain addition reactions as well as a catalyst for the conjugate addition process is proposed.

Original languageEnglish
Pages (from-to)1863-1871
Number of pages9
JournalTetrahedron
Volume63
Issue number8
DOIs
Publication statusPublished - 2007 Feb 19

Fingerprint

Addition reactions
Ketones
Sulfhydryl Compounds
Free Radicals
Derivatives
Catalysts
ceric ammonium nitrate
benzeneselenol
ammonium nitrate

Keywords

  • 1,4-Addition
  • Ceric ammonium nitrate (CAN)
  • Solvent free
  • Thiol and benzeneselenol
  • α,β-Unsaturated ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Ceric ammonium nitrate (CAN) as a green and highly efficient promoter for the 1,4-addition of thiols and benzeneselenol to α,β-unsaturated ketones. / Chu, Cheng Ming; Gao, Shijay; Sastry, M. N.V.; Kuo, Chun Wei; Lu, Chaowei; Liu, Ju Tsung; Yao, Ching-Fa.

In: Tetrahedron, Vol. 63, No. 8, 19.02.2007, p. 1863-1871.

Research output: Contribution to journalArticle

Chu, Cheng Ming ; Gao, Shijay ; Sastry, M. N.V. ; Kuo, Chun Wei ; Lu, Chaowei ; Liu, Ju Tsung ; Yao, Ching-Fa. / Ceric ammonium nitrate (CAN) as a green and highly efficient promoter for the 1,4-addition of thiols and benzeneselenol to α,β-unsaturated ketones. In: Tetrahedron. 2007 ; Vol. 63, No. 8. pp. 1863-1871.
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AU - Kuo, Chun Wei

AU - Lu, Chaowei

AU - Liu, Ju Tsung

AU - Yao, Ching-Fa

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