Literature DB >> 27072872

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

Yan-Long Zheng1, Yan-Yao Liu1, Yi-Mei Wu1, Yin-Xia Wang1, Yu-Tong Lin1, Mengchun Ye2,3.   

Abstract

An FeBr3 -catalyzed reductive coupling of various aldehydes with alkenes that proceeds through a direct hydride transfer pathway has been developed. With (i) PrOH as the hydrogen donor under mild conditions, previously challenging coupling reactions of unactivated alkyl and aryl aldehydes with simple alkenes, such as styrene derivatives and α-olefins, proceeded smoothly to furnish a diverse range of functionalized alcohols with complete linear regioselectivity.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aldehydes; alkenes; hydride transfer; iron; transfer hydrogenative couplings

Year:  2016        PMID： 27072872     DOI： 10.1002/anie.201602130

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


  9 in total

Review 1.  Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Authors:  Khoa D Nguyen; Boyoung Y Park; Tom Luong; Hiroki Sato; Victoria J Garza; Michael J Krische
Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

2.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

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

Authors:  Hongde Xiao; Gang Wang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-02       Impact factor: 15.336

4.  Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.

Authors:  Jichao Xiao; John Montgomery
Journal:  ACS Catal       Date:  2022-02-03       Impact factor: 13.700

5.  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

6.  Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical.

Authors:  Jia Cao; Guoqiang Wang; Liuzhou Gao; Xu Cheng; Shuhua Li
Journal:  Chem Sci       Date:  2018-02-28       Impact factor: 9.825

7.  Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes.

Authors:  Jing Li; Alexander Preinfalk; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

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.  Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds.

Authors:  Hyowon Seo; Timothy F Jamison
Journal:  Org Lett       Date:  2019-12-10       Impact factor: 6.005
  9 in total

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