Halide-free dehydrative allylation using allylic alcohols promoted by a palladium-triphenyl phosphite catalyst

被引：169

作者：

Kayaki, Y

Koda, T

Ikariya, T ^{[1
]}

机构：

[1] Japan Sci & Technol Agcy, PRESTO, Meguro Ku, Tokyo 1528552, Japan

[2] Tokyo Inst Technol, Grad Sch Sci & Engn, Meguro Ku, Tokyo 1528552, Japan

[3] Tokyo Inst Technol, Frontier Collaborat Res Ctr, Meguro Ku, Tokyo 1528552, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 07期

关键词：

D O I：

10.1021/jo030370g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The triphenyl phosphite-palladium complex was found to effect catalytic substitution reactions of allylic alcohols via a direct C-O bond cleavage. The dehydrative etherification proceeded efficiently without any cocatalysts and bases to give allylic ethers in good to excellent yields.

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收藏

页码：2595 / 2597

页数：3

相关论文

共 32 条

[1]

ATKINS KE, 1970, TETRAHEDRON LETT, V43, P3821

[2] ALKYLATION OF ACTIVE METHYLENE-COMPOUNDS BY ALLYLIC ALCOHOLS USING TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) CATALYSTS [J].

BERGBREITER, DE ;

WEATHERFORD, DA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :883-884

[3] Nickel vs. palladium catalysts for coupling reactions of allyl alcohol with soft nucleophiles: activities and deactivation processes [J].

Bricout, H ;

Carpentier, JF ;

Mortreux, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 136 (03) :243-251

[4]

Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585

[5] PALLADIUM-CATALYZED REACTION OF ARYL-SUBSTITUTED ALLYLIC ALCOHOLS WITH ZINC ENOLATES OF BETA-DICARBONYL COMPOUNDS IN THE PRESENCE OF TITANIUM(IV) ISOPROPOXIDE [J].

ITOH, K ;

HAMAGUCHI, N ;

MIURA, M ;

NOMURA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21) :2833-2835

[6] Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids [J].

Kabalka, GW ;

Dong, G ;

Venkataiah, B .

ORGANIC LETTERS, 2003, 5 (06) :893-895

[7] Pd•Et3B-catalyzed alkylation of amines with allylic alcohols [J].

Kimura, M ;

Futamata, M ;

Shibata, K ;

Tamaru, Y .

CHEMICAL COMMUNICATIONS, 2003, (02) :234-235

[8] Et3B-Pd-promoted allylation of benzaldehyde with allylic alcohols [J].

Kimura, M ;

Tomizawa, T ;

Horino, Y ;

Tanaka, S ;

Tamaru, Y .

TETRAHEDRON LETTERS, 2000, 41 (19) :3627-3629

[9] Strikingly simple direct α-allylation of aldehydes with allyl alcohols:: Remarkable advance in the Tsuji-Trost reaction [J].

Kimura, M ;

Horino, Y ;

Mukai, R ;

Tanaka, S ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10401-10402

[10] PALLADIUM AND ARSENIC(III) OXIDE-CATALYZED ALLYLIC ALKYLATION BY ALLYLIC ALCOHOLS UNDER NEUTRAL CONDITIONS [J].

LU, XY ;

LU, L ;

SUN, JH .

JOURNAL OF MOLECULAR CATALYSIS, 1987, 41 (1-2) :245-251

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