Catalytic intermolecular Pauson-Khand-type reaction: Strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction

被引：46

作者：

Itami, K ^{[1
]}

Mitsudo, K ^{[1
]}

Fujita, K ^{[1
]}

Ohashi, Y ^{[1
]}

Yoshida, J ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 35期

关键词：

D O I：

10.1021/ja047484+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Some circumstantial evidence for the directing effect of the 2-pyridylsilyl group in the Ru-catalyzed intermolecular Pauson-Khand-type reaction (PKR) of alkenyl(2-pyridyl)silane, alkyne, and carbon monoxide has been provided. Most importantly, we have succeeded in isolating several monometallic Ru complexes relevant to the catalytic reaction: Ru(vinylsilane)(CO)(3) complexes and ruthenacyclopentene. While the stoichimetric reaction of the Ru(vinylsilane)(CO)(3) complex with an alkyne led to the formation of the corresponding cyclopentenone (PKR product) at 100 degreesC, the ruthenacyclopentene intermediate was quantitatively produced at 50 degreesC. This complex was also converted to a cyclopentenone upon heating at 100 degreesC. Moreover, it was also found that the Ru(vinylsilane)(CO)(3) complex and ruthenacyclopentene serve as catalysts in intermolecular PKR.

引用

页码：11058 / 11066

页数：9

共 165 条

[1] The tert-butylsulfinyl group as a highly efficient chiral auxiliary in asymmetric Pauson-Khand reactions [J].

Adrio, J ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7411-7412

[2] Pauson-Khand reaction of activated olefins. [J].

Ahmar, M ;

Antras, F ;

Cazes, B .

TETRAHEDRON LETTERS, 1999, 40 (30) :5503-5506

[3]

Alami M, 2002, ANGEW CHEM INT EDIT, V41, P1578, DOI 10.1002/1521-3773(20020503)41:9<1578::AID-ANIE1578>3.0.CO

[4]

2-C

[5] STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].

BEAK, P ;

MEYERS, AI .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363

[6] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].

Beak, P ;

Basu, A ;

Gallagher, DJ ;

Park, YS ;

Thayumanavan, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560

[7] Thermal promotion of the cobalt catalyzed intramolecular Pauson-Khand reaction - An alternative experimental protocol for cyclopentenone synthesis [J].

Belanger, DB ;

O'Mahony, DJR ;

Livinghouse, T .

TETRAHEDRON LETTERS, 1998, 39 (42) :7637-7640

[8] Hexacarbonyldicobalt-alkyne complexes as convenient Co2(CO)8 surrogates in the catalytic Pauson-Khand reaction [J].

Belanger, DB ;

Livinghouse, T .

TETRAHEDRON LETTERS, 1998, 39 (42) :7641-7644

[9] OLEFINIC TERTIARY PHOSPHINE COMPLEXES OF IRON AND RUTHENIUM - COUPLING AND DEHYDROGENATION OF VINYL GROUPS IN COORDINATION SPHERE OF A RUTHENIUM COMPLEX [J].

BENNETT, MA ;

JOHNSON, RN ;

TOMKINS, IB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (01) :61-69

[10] DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION [J].

BERK, SC ;

GROSSMAN, RB ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8593-8601

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