Indium(I) bromide-mediated regioselective Markovnikov hydroselenation, diselenation and hydration of terminal alkynes with diphenyldiselenide in aqueous media

被引：22

作者：

Peppe, C ^{[1
]}

Lang, ES ^{[1
]}

Ledesma, GN ^{[1
]}

de Castro, LB ^{[1
]}

Barros, OSD ^{[1
]}

Mello, PD ^{[1
]}

机构：

[1] UFSM, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

来源：

SYNLETT | 2005年 / 20期

关键词：

indium(I) bromide; diphenyidiselenide; vinyl selenides; vinyl diselenides; hydration of alkynes; aqueous media;

D O I：

10.1055/s-2005-921931

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The indium(III) selenolate obtained from indium(l) bromide and diphenyldiselenide promotes, alternatively, the Markovnikov hydroselenation, diselenation or hydration of terminal alkynes, depending on the experimental conditions.

引用

页码：3091 / 3094

页数：4

共 21 条

[1] Palladium and platinum catalyzed hydroselenation of alkynes: Se-H vs Se-Se addition to CC bond [J].

Ananikov, VP ;

Malyshev, DA ;

Beletskaya, IP ;

Aleksandrov, GG ;

Eremenko, IL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 679 (02) :162-172

[2] Indium(I) iodide-mediated regioselective ring opening of epoxides with diphenyldiselenide:: The preparation of β-hydroxy selenides [J].

Barros, OSD ;

de Carvalho, AB ;

Lang, ES ;

Peppe, C .

LETTERS IN ORGANIC CHEMISTRY, 2004, 1 (01) :43-46

[3] Indium(I) iodide-mediated chemo-, regio-, and stereoselective hydrotelluration of 2-alkyn-1-ol derivatives [J].

Barros, OSD ;

Lang, ES ;

Peppe, C ;

Zeni, G .

SYNLETT, 2003, (11) :1725-1727

[4]

Barros OSD, 2002, TETRAHEDRON LETT, V43, P7921

[5] HOMOGENEOUSLY CATALYZED HYDRATION OF ACETYLENES BY MERCURIC PERCHLORATE-PERCHLORIC ACID - EVIDENCE FOR A BIS-(ACETYLENE)-MERCURIC ION COMPLEX AS AN INTERMEDIATE [J].

BUDDE, WL ;

DESSY, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (24) :3964-&

[6] Organometallic gold(III) compounds as catalysts for the addition of water and methanol to terminal alkynes [J].

Casado, R ;

Contel, M ;

Laguna, M ;

Romero, P ;

Sanz, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11925-11935

[7] THE 1ST EXAMPLE OF TRANSITION-METAL-CATALYZED HYDROSELENATION OF ACETYLENES [J].

KUNIYASU, H ;

OGAWA, A ;

SATO, KI ;

RYU, I ;

SONODA, N .

TETRAHEDRON LETTERS, 1992, 33 (38) :5525-5528

[8] Single source molecular precursors for the deposition of III/VI chalcogenide semiconductors by MOCVD and related techniques [J].

Lazell, M ;

O'Brien, P ;

Otway, DJ ;

Park, JH .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (24) :4479-4486

[9] PHENYL SELENIDE ANION, A SUPERIOR REAGENT FOR THE SN2 CLEAVAGE OF ESTERS AND LACTONES [J].

LIOTTA, D ;

SUNAY, U ;

SANTIESTEBAN, H ;

MARKIEWICZ, W .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (13) :2605-2610

[10] Insight into the selective room-temperature platinum(II) catalytic hydration of alkynes in water [J].

Lucey, DW ;

Atwood, JD .

ORGANOMETALLICS, 2002, 21 (12) :2481-2490

← 1 2 3 →