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Literature DB >> 25757459

Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination.

Brannon Sam¹, Tom Luong, Michael J Krische.

Abstract

Ruthenium(II) complexes catalyze the CC coupling of 1,1-disubstituted allenes and fluorinated alcohols to form homoallylic alcohols bearing all-carbon quaternary centers with good to complete levels of diastereoselectivity. Whereas fluorinated alcohols are relatively abundant and tractable, the corresponding aldehydes are often not commercially available because of their instability.

Entities: Chemical Gene

Keywords: allylic compounds; diastereoselectivity; fluorine; hydrogenation; ruthenium

Mesh：

Substances：

Year: 2015 PMID： 25757459 PMCID： PMC4405479 DOI： 10.1002/anie.201500238

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

21 in total

Review 1. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors: Jun-An Ma; Dominique Cahard
Journal: Chem Rev Date: 2004-12 Impact factor: 60.622

2. Some typical advances in the synthetic applications of allenes.

Authors: Shengming Ma
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

3. Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors: Jun-An Ma; Dominique Cahard
Journal: Chem Rev Date: 2008-09 Impact factor: 60.622

4. Iridium-catalysed direct C-C coupling of methanol and allenes.

Authors: Joseph Moran; Angelika Preetz; Ryan A Mesch; Michael J Krische
Journal: Nat Chem Date: 2011-02-27 Impact factor: 24.427

Review 5. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

6. Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.

Authors: Christopher D Grant; Michael J Krische
Journal: Org Lett Date: 2009-10-15 Impact factor: 6.005

7. Enantioselective carbonyl reverse prenylation from the alcohol or aldehyde oxidation level employing 1,1-dimethylallene as the prenyl donor.

Authors: Soo Bong Han; In Su Kim; Hoon Han; Michael J Krische
Journal: J Am Chem Soc Date: 2009-05-27 Impact factor: 15.419

Review 8. Allenamides: a powerful and versatile building block in organic synthesis.

Authors: Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2013-04-04 Impact factor: 60.622

Review 9. Fluorine in pharmaceuticals: looking beyond intuition.

Authors: Klaus Müller; Christoph Faeh; François Diederich
Journal: Science Date: 2007-09-28 Impact factor: 47.728

10. Ruthenium catalyzed reductive coupling of paraformaldehyde to trifluoromethyl allenes: CF3-bearing all-carbon quaternary centers.

Authors: Brannon Sam; T Patrick Montgomery; Michael J Krische
Journal: Org Lett Date: 2013-07-10 Impact factor: 6.005

13 in total

1. 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

2. Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through Co^III -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors: Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal: Angew Chem Int Ed Engl Date: 2019-08-01 Impact factor: 15.336

3. Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors: James Roane; Michael Holmes; Michael J Krische
Journal: Curr Opin Green Sustain Chem Date: 2017-06-09

Review 4. 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

5. A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors: Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2018-02-02 Impact factor: 15.419

6. Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

Authors: Tao Liang; Wandi Zhang; Te-Yu Chen; Khoa D Nguyen; Michael J Krische
Journal: J Am Chem Soc Date: 2015-09-29 Impact factor: 15.419

7. Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors: Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal: J Am Chem Soc Date: 2019-01-25 Impact factor: 15.419

Review 8. Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors: Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal: Chem Rev Date: 2018-06-13 Impact factor: 60.622

9. Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling.

Authors: Gilmar A Brito; Franco Della-Felice; Guoshun Luo; Alexander S Burns; Ronaldo A Pilli; Scott D Rychnovsky; Michael J Krische
Journal: Org Lett Date: 2018-06-25 Impact factor: 6.005

Review 10. Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors: Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal: Chemistry Date: 2021-07-29 Impact factor: 5.020