Literature DB >> 27910228

Regioselective Hydrohydroxyalkylation of Styrene with Primary Alcohols or Aldehydes via Ruthenium-Catalyzed C-C Bond Forming Transfer Hydrogenation.

Hongde Xiao1, Gang Wang1, Michael J Krische1.   

Abstract

Transfer hydrogenative coupling of styrene with primary alcohols using the precatalyst HClRu(CO)(PCy3 )2 modified by AgOTf or HBF4 delivers branched or linear adducts from benzylic or aliphatic alcohols, respectively. Related 2-propanol mediated reductive couplings also are described.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond formation; cross-coupling; homogenous catalysis; hydrogenation; ruthenium

Mesh：

Substances：

Year:  2016        PMID： 27910228      PMCID： PMC5189692          DOI： 10.1002/anie.201609056

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


  12 in total

1.  Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene.

Authors:  Jason R Zbieg; Eiji Yamaguchi; Emma L McInturff; Michael J Krische
Journal:  Science       Date:  2012-03-22       Impact factor: 47.728

2.  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

3.  Osmium(0)-Catalyzed C-C Coupling of Ethylene and α-Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Org Chem       Date:  2016-09-08       Impact factor: 4.354

4.  Ruthenium-catalyzed reductive coupling of 1,3-enynes and aldehydes by transfer hydrogenation: anti-diastereoselective carbonyl propargylation.

Authors:  Laina M Geary; Joyce C Leung; Michael J Krische
Journal:  Chemistry       Date:  2012-11-12       Impact factor: 5.236

5.  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

6.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

7.  Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of beta,gamma-unsaturated ketones.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

Review 8.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

9.  Iron-Catalyzed Regioselective Transfer Hydrogenative Couplings of Unactivated Aldehydes with Simple Alkenes.

Authors:  Yan-Long Zheng; Yan-Yao Liu; Yi-Mei Wu; Yin-Xia Wang; Yu-Tong Lin; Mengchun Ye
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-13       Impact factor: 15.336

10.  Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.

Authors:  Jeffrey S Bandar; Erhad Ascic; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419
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  6 in total

1.  Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.

Authors:  Jack Twilton; Melodie Christensen; Daniel A DiRocco; Rebecca T Ruck; Ian W Davies; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-06       Impact factor: 15.336

Review 2.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

3.  Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate.

Authors:  Robert A Swyka; William G Shuler; Brian J Spinello; Wandi Zhang; Chunling Lan; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-04-18       Impact factor: 15.419

4.  Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.

Authors:  Brian J Spinello; Jessica Wu; Yoon Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

5.  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

6.  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
  6 in total

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