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

doi:10.1016/j.tet.2006.12.018

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^*

^*Corresponding author for this work

Department of Chemistry

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

55 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 language	English
Pages (from-to)	1863-1871
Number of pages	9
Journal	Tetrahedron
Volume	63
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2006.12.018
Publication status	Published - 2007 Feb 19

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

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10.1016/j.tet.2006.12.018

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title = "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",

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.",

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

author = "Chu, {Cheng Ming} and Shijay Gao and Sastry, {M. N.V.} and Kuo, {Chun Wei} and Chaowei Lu and Liu, {Ju Tsung} and Yao, {Ching Fa}",

note = "Funding Information: Financial support of this work by the National Science Council of the Republic of China and National Taiwan Normal University (ORD93-C) is gratefully acknowledged. ",

year = "2007",

month = feb,

day = "19",

doi = "10.1016/j.tet.2006.12.018",

language = "English",

volume = "63",

pages = "1863--1871",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - 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

AU - Chu, Cheng Ming

AU - Gao, Shijay

AU - Sastry, M. N.V.

AU - Kuo, Chun Wei

AU - Lu, Chaowei

AU - Liu, Ju Tsung

AU - Yao, Ching Fa

N1 - Funding Information: Financial support of this work by the National Science Council of the Republic of China and National Taiwan Normal University (ORD93-C) is gratefully acknowledged.

PY - 2007/2/19

Y1 - 2007/2/19

N2 - 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.

AB - 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.

KW - 1,4-Addition

KW - Ceric ammonium nitrate (CAN)

KW - Solvent free

KW - Thiol and benzeneselenol

KW - α,β-Unsaturated ketones

UR - http://www.scopus.com/inward/record.url?scp=33846264046&partnerID=8YFLogxK

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U2 - 10.1016/j.tet.2006.12.018

DO - 10.1016/j.tet.2006.12.018

M3 - Article

AN - SCOPUS:33846264046

SN - 0040-4020

VL - 63

SP - 1863

EP - 1871

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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