Literature DB >> 24123602

[3]Dendralene synthesis: rhodium(III)-catalyzed alkenyl C-H activation and coupling reaction with allenyl carbinol carbonate.

Honggen Wang1, Bernhard Beiring, Da-Gang Yu, Karl D Collins, Frank Glorius.   

Abstract

[3]DendrAl(l)ene! A new synthesis of [3]dendralenes is based on a Rh(III) -catalyzed alkenyl CH activation and coupling reaction with allenyl carbinol carbonates (see scheme; DG=directing group). A variety of [3]dendralenes with diverse substitution patterns are accessible with good efficiency. The reaction is highly stereoselective and compatible with different directing groups and numerous functional groups.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC coupling; CH activation; [3]dendralenes; dienes; trienes

Year:  2013        PMID: 24123602     DOI: 10.1002/anie.201306754

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


  10 in total

1.  Application of a robustness screen for the evaluation of synthetic organic methodology.

Authors:  Karl D Collins; Andreas Rühling; Frank Glorius
Journal:  Nat Protoc       Date:  2014-05-15       Impact factor: 13.491

2.  Rhodium(III)-Catalyzed Allylic C(sp(3))-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

Authors:  Alexis Archambeau; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-11       Impact factor: 15.336

3.  Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhao Wu; Nina Fatuzzo; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2020-02-03       Impact factor: 15.419

4.  An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation.

Authors:  Kate D Otley; Jonathan A Ellman
Journal:  Org Lett       Date:  2015-02-25       Impact factor: 6.005

5.  Palladium/norbornene-catalyzed distal alkenyl C-H arylation and alkylation of cis-olefins.

Authors:  Zhao Wu; Nina Fatuzzo; Guangbin Dong
Journal:  Tetrahedron       Date:  2021-05-11       Impact factor: 2.388

6.  Pd-Catalyzed Heck-Type Reactions of Allenes for Stereoselective Syntheses of Substituted 1,3-Dienes.

Authors:  Logan E Vine; Jennifer M Schomaker
Journal:  Chemistry       Date:  2021-11-11       Impact factor: 5.236

7.  Rh(iii)-Catalyzed [5 + 1] annulation of 2-alkenylanilides and 2-alkenylphenols with allenyl acetates.

Authors:  Anurag Singh; Rahul K Shukla; Chandra M R Volla
Journal:  Chem Sci       Date:  2022-01-19       Impact factor: 9.825

8.  Synthesis of Cross-Conjugated Polyenes via Palladium-Catalyzed Oxidative C-C Bond Forming Cascade Reactions of Allenes.

Authors:  Veluru Ramesh Naidu; Jan-E Bäckvall
Journal:  J Org Chem       Date:  2020-04-02       Impact factor: 4.354

9.  A general synthesis of dendralenes.

Authors:  Josemon George; Jas S Ward; Michael S Sherburn
Journal:  Chem Sci       Date:  2019-09-12       Impact factor: 9.825

10.  Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.

Authors:  Haoqiang Zhao; Xin Xu; Zhenli Luo; Lei Cao; Bohan Li; Huanrong Li; Lijin Xu; Qinghua Fan; Patrick J Walsh
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825

  10 in total

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