Literature DB >> 19156265

Transition metal catalysed reactions of alcohols using borrowing hydrogen methodology.

Tracy D Nixon1, Michael K Whittlesey, Jonathan M J Williams.   

Abstract

The reactivity of alcohols can be enhanced by the temporary removal of hydrogen using a transition metal catalyst to generate an intermediate aldehyde or ketone. The so-formed carbonyl compound has a greater reactivity towards nucleophilic addition accommodating the in situ formation of imines or alkenes. The return of hydrogen from the catalyst leads to the formation of new C-N and C-C bonds, often with water as the only reaction by-product.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 19156265     DOI: 10.1039/b813383b

Source DB:  PubMed          Journal:  Dalton Trans        ISSN: 1477-9226            Impact factor:   4.390


  27 in total

1.  Allenamide hydro-hydroxyalkylation: 1,2-amino alcohols via ruthenium-catalyzed carbonyl anti-aminoallylation.

Authors:  Jason R Zbieg; Emma L McInturff; Michael J Krische
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

2.  Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.

Authors:  Joyce C Leung; Ryan L Patman; Brannon Sam; Michael J Krische
Journal:  Chemistry       Date:  2011-09-27       Impact factor: 5.236

3.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

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

Authors:  Joseph Moran; Michael J Krische
Journal:  Pure Appl Chem       Date:  2012-03-13       Impact factor: 2.453

5.  Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors:  Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

6.  Diols as Dienophiles: Bridged Carbocycles via Ruthenium(0)-Catalyzed Transfer Hydrogenative Cycloadditions of Cyclohexadiene or Norbornadiene.

Authors:  Hiroki Sato; Keisuke Fukaya; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

7.  Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes.

Authors:  James M Cabrera; Johannes Tauber; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-04       Impact factor: 15.336

8.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

9.  Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes: carbonyl syn-crotylation from the alcohol oxidation level.

Authors:  Jason R Zbieg; Joseph Moran; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-06-16       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

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.