Literature DB >> 23722271

Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: byproduct-free prenylation of hydantoins.

Daniel C Schmitt1, Jungyong Lee, Anne-Marie R Dechert-Schmitt, Eiji Yamaguchi, Michael J Krische.   

Abstract

The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2)2] promotes the direct C-C coupling of isoprene with aryl substituted hydantoins 1a–1f at the diene C4-position to furnish products of n-prenylation 2a–2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative coupling to furnish a transient aza-ruthencyclopentene is proposed.

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Year:  2013        PMID： 23722271      PMCID： PMC3730527          DOI： 10.1039/c3cc43463j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  25 in total

1.  Ir(I)-catalyzed enantioselective secondary sp3 C-H bond activation of 2-(alkylamino)pyridines with alkenes.

Authors:  Shiguang Pan; Kohei Endo; Takanori Shibata
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

2.  [Ind2TiMe2]: a catalyst for the hydroaminomethylation of alkenes and styrenes.

Authors:  Raphael Kubiak; Insa Prochnow; Sven Doye
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-29       Impact factor: 15.336

3.  Aminopyridinato titanium catalysts for the hydroaminoalkylation of alkenes and styrenes.

Authors:  Jaika Dörfler; Sven Doye
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-12       Impact factor: 15.336

4.  Ru(3)(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes.

Authors:  N Chatani; T Asaumi; S Yorimitsu; T Ikeda; F Kakiuchi; S Murai
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

5.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

6.  Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

Authors:  Zigang Li; Junliang Zhang; Chad Brouwer; Cai-Guang Yang; Nicholas W Reich; Chuan He
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

7.  Selective C-H activation alpha to primary amines. Bridging metallaaziridines for catalytic, intramolecular alpha-alkylation.

Authors:  Jason A Bexrud; Patrick Eisenberger; David C Leitch; Philippa R Payne; Laurel L Schafer
Journal:  J Am Chem Soc       Date:  2009-02-18       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

9.  Cationic Ir(I)-Catalyzed sp(3) C-H Bond Alkenylation of Amides with Alkynes.

Authors:  Kyoji Tsuchikama; Mitsugu Kasagawa; Kohei Endo; Takanori Shibata
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

10.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419
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  9 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Regioselective Arylboration of Isoprene and Its Derivatives by Pd/Cu Cooperative Catalysis.

Authors:  Kevin B Smith; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

Review 3.  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

4.  Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

5.  α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Authors:  Jillian E Spangler; Yoshihisa Kobayashi; Pritha Verma; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-09-10       Impact factor: 15.419

6.  Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Authors:  Xinxin Shao; Kangnan Li; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-05-30       Impact factor: 15.419

Review 7.  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

8.  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

9.  Intermolecular Hydroaminoalkylation of Propadiene.

Authors:  Tobias Kaper; Malte Fischer; Michael Warsitz; René Zimmering; Ruediger Beckhaus; Sven Doye
Journal:  Chemistry       Date:  2020-10-01       Impact factor: 5.236
  9 in total

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