Rhodium-catalyzed isomerization of α-arylpropargyl alcohols to indanones:: Involvement of an unexpected reaction cascade

被引：104

作者：

Shintani, R ^{[1
]}

Okamoto, K ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 09期

关键词：

D O I：

10.1021/ja042582g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-catalyzed isomerization of α-arylpropargyl alcohols to indanones has been developed under mild conditions. Considering the ease of preparation of these propargyl alcohols (terminal alkynes + aromatic aldehydes), this method provides a new way of constructing indanones with high efficiency. By the mechanistic investigations using deuterium-labeled substrates, it has also been demonstrated that the reaction goes through an unexpected cascade, with a 1,4-hydrogen shift being the turnover-limiting step of the catalytic cycle. Copyright © 2005 American Chemical Society.

引用

页码：2872 / 2873

页数：2

共 19 条

[1] Intermolecular C-H activation of hydrocarbons by tungsten alkylidene complexes: An experimental and computational mechanistic study [J].

Adams, CS ;

Legzdins, P ;

McNeil, WS .

ORGANOMETALLICS, 2001, 20 (23) :4939-4955

[2] Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts [J].

Fairlamb, IJS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1048-1052

[3] A SIMPLE AND CONVENIENT PREPARATION OF [(PH(3)P)(4)RH-2(MU-OH)(2)] AND ITS REACTIONS WITH C-H, O-H, AND M-H ACIDS [J].

GRUSHIN, VV ;

KUZNETSOV, VF ;

BENSIMON, C ;

ALPER, H .

ORGANOMETALLICS, 1995, 14 (08) :3927-3932

[4]

GUO C, 1992, SYNLETT, P405

[5] PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems [J].

Harrak, Y ;

Blaszykowski, C ;

Bernard, M ;

Cariou, K ;

Mainetti, E ;

Mouriès, V ;

Dhimane, AL ;

Fensterbank, L ;

Malacria, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8656-8657

[6] Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].

Hayashi, T ;

Takahashi, M ;

Takaya, Y ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058

[7] Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].

Hayashi, T ;

Inoue, K ;

Taniguchi, N ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919

[8]

LU XY, 1992, J ORGANOMET CHEM, V428, P259

[9] A SIMPLE ROUTE TO ALPHA,BETA-UNSATURATED ALDEHYDES FROM PROP-2-YNOLS [J].

MA, D ;

LU, XY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :890-891

[10] ISOMERIZATION OF PROPARGYLIC ALCOHOLS CATALYZED BY AN IRIDIUM COMPLEX [J].

MA, DW ;

LU, XY .

TETRAHEDRON LETTERS, 1989, 30 (16) :2109-2112

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