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

被引：49
作者：
Chu, Cheng-Ming [1 ]
Gao, Shijay [1 ]
Sastry, M. N. V. [1 ]
Kuo, Chun-Wei [1 ]
Lu, Chaowei [1 ]
Liu, Ju-Tsung [1 ]
Yao, Ching-Fa [1 ]
机构：
[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan
来源：
TETRAHEDRON | 2007年 / 63卷 / 08期
关键词：
1,4-addition; thiol and benzeneselenol; alpha; beta-unsaturated ketones; solvent free; ceric ammonium nitrate (CAN);
D O I：
10.1016/j.tet.2006.12.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and efficient process for the 1,4-addition of thiols and benzeneselenols to various alpha-beta-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 alpha,beta-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. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1863 / 1871
页数：9
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