Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides

被引：12
作者：
Bouchet, Lydia M. [1 ]
Penenory, Alicia B. [1 ]
Argueello, Juan E. [1 ]
机构：
[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC, RA-5000 Cordoba, Argentina
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 09期
关键词：
Selenides; S(RN)1; Photochemistry; Electron transfer; Radical; UNSYMMETRICAL DIORGANYL SELENIDES; PRIMARY SELENOCARBOXYLIC AMIDES; ORGANOSELENIUM CHEMISTRY; NUCLEOPHILIC-SUBSTITUTION; ORGANOTELLURIUM COMPOUNDS; DIPHENYL DISELENIDE; EFFICIENT SYNTHESIS; MEDIATED CLEAVAGE; ALKYL-HALIDES; DIARYL;
D O I：
10.1016/j.tetlet.2010.11.115
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Selenobenzamide (-SeCNH(Ph), 1), selenourea (-SeCNH(NH2), 2) and selenocyanate (-SeCN, 3) anions afford areneselenolate ions (ArSe-) under photostimulation in the presence of tert-butoxide or 2-naphthoxide ions as electron donors (entrainment conditions) in DMSO. In a 'one-pot' procedure, ArSe- anions can be trapped by a subsequent aliphatic nucleophilic substitution giving aryl methyl selenides in good to excellent yields (67-100%). This simple approach is compatible with electron-donating and electron-withdrawing substituents, such as nitro and carbonyl groups. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：969 / 972
页数：4
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