Ruthenium complex-catalyzed anti-Markovnikov hydration of terminal alkynes

被引：149

作者：

Suzuki, T

Tokunaga, M

Wakatsuki, Y ^{[1
]}

机构：

[1] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan

[2] Japan Sci & Technol Corp, PRESTO, Wako, Saitama 3510198, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 05期

关键词：

D O I：

10.1021/ol0003937

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Highly regioselective, efficient, acid substituent-tolerant anti-Markovnikov hydration of terminal alkynes occurs to give n-aldehyde by use of a catalytic amount of easily available cyclopentadienylruthenium complexes bearing appropriate bidentate or monodentate phosphine ligands, Typically, RuCpCl(dppm) (1 mol %) catalyzes the addition of water to 1-hexyne at 100 degreesC to give hexanal in 95% yield: 2-hexanone is not detected at all.

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页码：735 / 737

页数：3

相关论文

共 18 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2] Hydration of alkynes by a PtCl4-CO catalyst [J].

Baidossi, W ;

Lahav, M ;

Blum, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :669-672

[3] The mechanism of the Ru-assisted C-C bond cleavage of terminal alkynes by water [J].

Bianchini, C ;

Casares, JA ;

Peruzzini, M ;

Romerosa, A ;

Zanobini, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (19) :4585-4594

[4] ALKYNE HYDRATION PROMOTED BY RHCL3 AND QUATERNARY AMMONIUM-SALTS [J].

BLUM, J ;

HUMINER, H ;

ALPER, H .

JOURNAL OF MOLECULAR CATALYSIS, 1992, 75 (02) :153-160

[5] CYCLOPENTADIENYL-RUTHENIUM AND CYCLOPENTADIENYL-OSMIUM CHEMISTRY .10. REACTIONS OF VINYLIDENE COMPLEXES WITH ALCOHOLS AND WATER - SYNTHESES OF ALKOXY(ALKYL)CARBENE, ACYL AND ALKYL COMPLEXES [J].

BRUCE, MI ;

SWINCER, AG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (07) :1471-1483

[6] EFFECTIVE TRANSFORMATION OF UNACTIVATED ALKYNES INTO KETONES OR ACETALS BY MEANS OF AU(III) CATALYST [J].

FUKUDA, Y ;

UTIMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3729-3731

[7] FORMATION AND PROPERTIES OF SOME CHLORACARBONYL COMPLEXES OF RUTHENIUM (2) AND RUTHENIUM(3) [J].

HALPERN, J ;

JAMES, BR ;

KEMP, ALW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (22) :5142-&

[8] CATALYSIS OF HYDRATION OF ACETYLENIC COMPOUNDS BY RUTHENIUM(III) CHLORIDE [J].

HALPERN, J ;

JAMES, BR ;

KEMP, ALW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (19) :4097-&

[9] CATALYTIC HYDRATION OF ALKYNES WITH PLATINUM(II) COMPLEXES [J].

HARTMAN, JW ;

HISCOX, WC ;

JENNINGS, PW .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7613-7614

[10] CATALYTIC HYDRATION OF ALKYNES WITH ZEISE DIMER [J].

HISCOX, W ;

JENNINGS, PW .

ORGANOMETALLICS, 1990, 9 (07) :1997-1999