Literature DB >> 23430602

Formation of C-C bonds via ruthenium-catalyzed transfer hydrogenation().

Joseph Moran1, Michael J Krische.   

Abstract

Ruthenium-catalyzed transfer hydrogenation of diverse π-unsaturated reactants in the presence of aldehydes provides products of carbonyl addition. Dehydrogenation of primary alcohols in the presence of the same π-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.

Entities:  

Keywords:  C–C bond formation; catalysis; ruthenium catalysis; transfer hydrogenation

Year:  2012        PMID: 23430602      PMCID: PMC3575689          DOI: 10.1351/PAC-CON-11-10-18

Source DB:  PubMed          Journal:  Pure Appl Chem        ISSN: 0033-4545            Impact factor:   2.453


  51 in total

Review 1.  Non-metathesis ruthenium-catalyzed C-C bond formation.

Authors:  B M Trost; F D Toste; A B Pinkerton
Journal:  Chem Rev       Date:  2001-07       Impact factor: 60.622

Review 2.  Chiral allylic and allenic metal reagents for organic synthesis.

Authors:  James A Marshall
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354

3.  Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation.

Authors:  Jong-Rock Kong; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

4.  Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors:  Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

5.  Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

Authors: 
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

6.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

7.  Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

8.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

9.  Ruthenium hydride-catalyzed addition of aldehydes to dienes leading to beta,gamma-unsaturated ketones.

Authors:  Sohei Omura; Takahide Fukuyama; Jiro Horiguchi; Yuji Murakami; Ilhyong Ryu
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

10.  Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen: asymmetric synthesis of beta,gamma-unsaturated alpha-hydroxy esters.

Authors:  Young-Taek Hong; Chang-Woo Cho; Eduardas Skucas; Michael J Krische
Journal:  Org Lett       Date:  2007-08-18       Impact factor: 6.005

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  35 in total

1.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

Review 2.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

3.  Chiral-anion-dependent inversion of diastereo- and enantioselectivity in carbonyl crotylation via ruthenium-catalyzed butadiene hydrohydroxyalkylation.

Authors:  Emma L McInturff; Eiji Yamaguchi; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-12-12       Impact factor: 15.419

4.  Asymmetric synthesis: Relay catalysis at a boron centre.

Authors:  Valer Jeso; Glenn C Micalizio
Journal:  Nature       Date:  2013-02-14       Impact factor: 49.962

Review 5.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors:  Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal:  Top Curr Chem (Cham)       Date:  2016-05-30

6.  Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles.

Authors:  Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-11       Impact factor: 15.336

7.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

8.  Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Authors:  Takahiko Itoh; T Patrick Montgomery; Antonio Recio; Michael J Krische
Journal:  Org Lett       Date:  2014-01-14       Impact factor: 6.005

9.  Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation.

Authors:  David J Del Valle; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-07-17       Impact factor: 15.419

Review 10.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336

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