Literature DB >> 29068505

Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Hiroki Sato1, Ben W H Turnbull1, Keisuke Fukaya1, Michael J Krische1.   

Abstract

Merging the characteristics of transfer hydrogenation and carbonyl addition, a broad new class of ruthenium(0)-catalyzed cycloadditions has been developed. As discussed in this Minireview, fused or bridged bicyclic ring systems are accessible in a redox-independent manner in C-C bond-forming hydrogen transfer reactions of diols, α-ketols, or 1,2-diones with diverse unsaturated reactants.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; cycloaddition; diols; hydrogen transfer; ruthenium

Mesh：

Substances：

Year:  2018        PMID： 29068505      PMCID： PMC5842109          DOI： 10.1002/anie.201709916

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


  57 in total

1.  Transition Metal-Mediated Cycloaddition Reactions.

Authors:  Mark Lautens; Wolfgang Klute; William Tam
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Ruthenium-catalyzed intramolecular homo-diels-alder reaction of alkyne-tethered norbornadienes. An entry to fused angular triquinanes.

Authors:  Alphonse Tenaglia; Sylvain Gaillard
Journal:  Org Lett       Date:  2007-08-03       Impact factor: 6.005

Review 3.  Alkenes in [2+2+2] Cycloadditions.

Authors:  Gema Domínguez; Javier Pérez-Castells
Journal:  Chemistry       Date:  2016-02-25       Impact factor: 5.236

Review 4.  Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.

Authors:  Graham E Dobereiner; Robert H Crabtree
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  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

6.  Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Authors:  Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  Science       Date:  2017-08-25       Impact factor: 47.728

7.  Diols, α-Ketols, and Diones as 22π Components in [2+2+2] Cycloadditions of 1,6-Diynes via Ruthenium(0)-Catalyzed Transfer Hydrogenation.

Authors:  Hiroki Sato; Matthias Bender; Weijie Chen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-12-09       Impact factor: 15.419

8.  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

Review 9.  C-Alkylation of Ketones and Related Compounds by Alcohols: Transition-Metal-Catalyzed Dehydrogenation.

Authors:  Fei Huang; Zhuqing Liu; Zhengkun Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-07       Impact factor: 15.336

10.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419
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  7 in total

1.  Thermal Hetero-Diels-Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones.

Authors:  Thomas Wurm; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  J Org Chem       Date:  2017-11-22       Impact factor: 4.354

2.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

Review 3.  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

4.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419

Review 5.  Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Authors:  Rosalie S Doerksen; Tomáš Hodík; Guanyu Hu; Nancy O Huynh; William G Shuler; Michael J Krische
Journal:  Chem Rev       Date:  2021-02-12       Impact factor: 60.622

6.  Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction.

Authors:  Zachary A Kasun; Hiroki Sato; Jing Nie; Yasuyuki Mori; Jon A Bender; Sean T Roberts; Michael J Krische
Journal:  Chem Sci       Date:  2018-08-30       Impact factor: 9.825

7.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  7 in total

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