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

页码：969 / 972

页数：4

共 68 条

[1] SELENIUM DERIVATIVES IN INDOLE SERIES .1. ON SYNTHESIS OF 3-SELENOCYANO-INDOLE AND 3,3-DIINDOLYL DISELENIDE [J].

AGENAS, LB .

ACTA CHEMICA SCANDINAVICA, 1963, 17 (01) :268-&

[2] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent [J].

Ajiki, K ;

Hirano, M ;

Tanaka, K .

ORGANIC LETTERS, 2005, 7 (19) :4193-4195

[3] Synthesis of novel Se-substituted selenocysteine derivatives as potential kidney selective prodrugs of biologically active selenol compounds: Evaluation of kinetics of beta-elimination reactions in rat renal cytosol [J].

Andreadou, I ;

Menge, WMPB ;

Commandeur, JNM ;

Worthington, EA ;

Vermeulen, NPE .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (10) :2040-2046

[4]

[Anonymous], 1999, ORGANOSELENIUM CHEM

[5]

[Anonymous], 2004, Chem. Heterocycl. Compd.

[6] NEW ROUTE TO ALKYL SELENOCYANATE FROM OLEFIN VIA HYDROBORATION - REACTION OF ORGANOBORANES WITH FERRIC SELENOCYANATE [J].

ARASE, A ;

MASUDA, Y .

CHEMISTRY LETTERS, 1976, (07) :785-788

[7] Quantum yields of the initiation step and chain propagation turnovers in SRN1 reactions:: Photostimulated reaction of 1-iodo-2-methyl-2 phenyl propane with carbanions in DMSO [J].

Argüello, JE ;

Peñéñory, AB ;

Rossi, RA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :7175-7182

[8] Reactivity of sulfur centered nucleophiles in photoinduced reactions with 1-bromonaphthalene [J].

Argüello, JE ;

Schmidt, LC ;

Peñéñory, AB .

ARKIVOC, 2003, :411-419

[9] One-Pot two-step synthesis of aryl sulfur compounds by photoinduced reactions of thiourea anion with aryl halides [J].

Arguello, JE ;

Schmidt, LC ;

Peñéñory, AB .

ORGANIC LETTERS, 2003, 5 (22) :4133-4136

[10] Al2O3-Supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A Protocol for the Synthesis of Unsymmetrical Diaryl and Alkyl Aryl Selenides [J].

Bhadra, Sukalyan ;

Saha, Amit ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4864-4867

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