Finding the proton in a key intermediate of anti-Markovnikov alkyne hydration by a bifunctional catalyst

被引：69

作者：

Grotjahn, Douglas B. ^{[1
]}

Kragulj, Elijah J. ^{[1
]}

Zeinalipour-Yazdi, Constantinos D. ^{[2
]}

Miranda-Soto, Valentin ^{[1
]}

Lev, Daniel A. ^{[1
]}

Cooksy, Andrew L. ^{[1
]}

机构：

[1] San Diego State Univ, Dept Chem & Biochem, San Diego, CA 92182 USA

[2] Univ Cyprus, Dept Chem, Heterogeneous Catalysis Lab, CY-1678 Nicosia, Cyprus

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 33期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ja803106z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The secondary structure of a bifunctional catalyst positions a crucial reactive proton in the final intermediate of anti-Markovnikov alkyne hydration to give an aldehyde. NMR coupling and isotopic labeling studies elucidate the location of this proton and its involvement in hydrogen bonding.

引用

页码：10860 / +

页数：3

共 25 条

[1] Geometrical features of hydrogen bonded complexes involving sterically hindered pyridines [J].

Andreeva, Daria V. ;

Ip, Brenda ;

Gurinov, Andrey A. ;

Tolstoy, Peter M. ;

Denisov, Gleb S. ;

Shenderovich, Ilja G. ;

Limbach, Hans-Heinrich .

JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (37) :10872-10879

[2]

Baur J, 2000, EUR J INORG CHEM, P1411

[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] 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

[5] Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].

Clapham, SE ;

Hadzovic, A ;

Morris, RH .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237

[6] Molecular recognition in homogeneous transition metal catalysis: a biomimetic strategy for high selectivity [J].

Das, Siddartha ;

Brudvig, Gary W. ;

Crabtree, Robert H. .

CHEMICAL COMMUNICATIONS, 2008, (04) :413-424

[7] Five-coordinate complex [RuHCl(CO)(PPr3i)(2)] as a precursor for the preparation of new cyclopentadienylruthenium compounds containing unsaturated eta(1)-carbon ligands [J].

Esteruelas, MA ;

Gomez, AV ;

Lahoz, FJ ;

Lopez, AM ;

Onate, E ;

Oro, LA .

ORGANOMETALLICS, 1996, 15 (15) :3423-3435

[8] Bifunctional organometallic catalysts involving proton transfer or hydrogen bonding [J].

Grotjahn, DB .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (24) :7146-7153

[9] A general bifunctional catalyst for the anti-Markovnikov hydration of terminal alkynes to aldehydes gives enzyme-like rate and selectivity enhancements [J].

Grotjahn, DB ;

Lev, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12232-12233

[10]

Grotjahn DB, 2001, ANGEW CHEM INT EDIT, V40, P3884, DOI 10.1002/1521-3773(20011015)40:20<3884::AID-ANIE3884>3.0.CO

← 1 2 3 →