Formation of C-C bonds via ruthenium-catalyzed transfer hydrogenation

被引：98

作者：

Moran, Joseph ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, 1 Univ Stn A5300, Austin, TX 78712 USA

来源：

PURE AND APPLIED CHEMISTRY | 2012年 / 84卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

C-C bond formation; catalysis; ruthenium catalysis; transfer hydrogenation; ALDEHYDE OXIDATION LEVEL; TRISUBSTITUTED ALLYLIC ALCOHOLS; FORMING TRANSFER HYDROGENATION; CARBONYL ALLYLATION; INTERMOLECULAR HYDROACYLATION; REDUCTIVE CYCLIZATION; REVERSE PRENYLATION; CONJUGATED ALKYNES; PI-ALLYLPALLADIUM; METAL REAGENTS;

D O I：

10.1351/PAC-CON-11-10-18

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ruthenium-catalyzed transfer hydrogenation of diverse p-unsaturated reactants in the presence of aldehydes provides products of carbonyl addition. Dehydrogenation of primary alcohols in the presence of the same p-unsaturated reactants provides identical products of carbonyl addition. In this way, carbonyl addition is achieved from the alcohol or aldehyde oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. In this account, the discovery of ruthenium-catalyzed C-C bond-forming transfer hydrogenations and the recent development of diastereo- and enantioselective variants are discussed.

引用

页码：1729 / 1739

页数：11

共 89 条

[1]

[Anonymous], J CHEM SOC CHEM COMM

[2] Synthetic variations based on low-valent chromium:: new developments [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Jiménez, JL ;

Palacios, JC .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (03) :169-177

[3] [Cr(Salen)] as a 'bridge' between asymmetric catalysis, Lewis acids and redox processes [J].

Bandini, M ;

Cozzi, PG ;

Umani-Ronchi, A .

CHEMICAL COMMUNICATIONS, 2002, (09) :919-927

[4] Divergent Regioselectivity in the Synthesis of Trisubstituted Allylic Alcohols by Nickel- and Ruthenium-Catalyzed Alkyne Hydrohydroxymethylation with Formaldehyde [J].

Bausch, Cory C. ;

Patman, Ryan L. ;

Breit, Bernhard ;

Krische, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) :5686-5689

[5] Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene [J].

Bower, John F. ;

Patman, Ryan L. ;

Krische, Michael J. .

ORGANIC LETTERS, 2008, 10 (05) :1033-1035

[6] Catalytic C-C coupling via transfer hydrogenation: Reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level [J].

Bower, John F. ;

Skucas, Eduardas ;

Patman, Ryan L. ;

Krische, Michael J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15134-+

[7] Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation [J].

Bower, John F. ;

Krische, Michael J. .

IRIDIUM CATALYSIS, 2011, 34 :107-138

[8] Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents [J].

Bower, John F. ;

Kim, In Su ;

Patman, Ryan L. ;

Krische, Michael J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :34-46

[9] New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings [J].

Chaulagain, Mani Raj ;

Sormunen, Grant J. ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) :9568-+

[10] α-hydroxy esters via enantioselective hydrogen-mediated C-C coupling:: Regiocontrolled reactions of silyl-substituted 1,3-diynes [J].

Cho, Chang-Woo ;

Krische, Michael J. .

ORGANIC LETTERS, 2006, 8 (17) :3873-3876

← 1 2 3 4 5 6 7 8 9 →