Literature DB >> 32243685

Enantioselective Pallada-Electrocatalyzed C-H Activation by Transient Directing Groups: Expedient Access to Helicenes.

Uttam Dhawa1, Cong Tian1, Tomasz Wdowik1, João C A Oliveira1, Jiping Hao1, Lutz Ackermann1,2.   

Abstract

Asymmetric pallada-electrocatalyzed C-H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective C-H activations were realized with high position-, diastereo-, and enantio-control under mild reaction conditions to obtain highly enantiomerically-enriched biaryls and fluorinated N-C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel chiral BINOLs, dicarboxylic acids and helicenes of value to asymmetric catalysis. Mechanistic studies by experiments and computation provided key insights into the catalyst's mode of action.
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Entities:  

Keywords:  asymmetric C−H activation; biaryls; helicene; palladium; transient directing group

Year:  2020        PMID: 32243685     DOI: 10.1002/anie.202003826

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


  13 in total

1.  C-H activation by immobilized heterogeneous photocatalysts.

Authors:  Isaac Choi; Julia Struwe; Lutz Ackermann
Journal:  Photochem Photobiol Sci       Date:  2021-11-16       Impact factor: 3.982

2.  Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

Authors:  Mixiang Tian; Lidong Shao; Xiaosan Su; Xuhong Zhou; Honglei Zhang; Kun Wei; Ruifen Sun; Junliang Wang
Journal:  RSC Adv       Date:  2022-06-27       Impact factor: 4.036

3.  Divergent rhodium-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes.

Authors:  Yi-Kang Xing; Xin-Ran Chen; Qi-Liang Yang; Shuo-Qing Zhang; Hai-Ming Guo; Xin Hong; Tian-Sheng Mei
Journal:  Nat Commun       Date:  2021-02-10       Impact factor: 14.919

Review 4.  Organic Electrochemistry: Molecular Syntheses with Potential.

Authors:  Cuiju Zhu; Nate W J Ang; Tjark H Meyer; Youai Qiu; Lutz Ackermann
Journal:  ACS Cent Sci       Date:  2021-03-09       Impact factor: 14.553

5.  Atropoenantioselective palladaelectro-catalyzed anilide C-H olefinations viable with natural sunlight as sustainable power source.

Authors:  Johanna Frey; Xiaoyan Hou; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

6.  Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations.

Authors:  Wen Wei; Alexej Scheremetjew; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

7.  Thioether-enabled palladium-catalyzed atroposelective C-H olefination for N-C and C-C axial chirality.

Authors:  Yanjun Li; Yan-Cheng Liou; Xinran Chen; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-03-10       Impact factor: 9.825

8.  PdII -Catalyzed C(alkenyl)-H Activation Facilitated by a Transient Directing Group.

Authors:  Mingyu Liu; Juntao Sun; Tuğçe G Erbay; Hui-Qi Ni; Raúl Martín-Montero; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-26       Impact factor: 16.823

9.  Distal Ruthenaelectro-Catalyzed meta-C-H Bromination with Aqueous HBr.

Authors:  Yulei Wang; Hendrik Simon; Xinran Chen; Zhipeng Lin; Shan Chen; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-16       Impact factor: 16.823

10.  Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary.

Authors:  Luca Buzzetti; Mikus Puriņš; Phillip D G Greenwood; Jerome Waser
Journal:  J Am Chem Soc       Date:  2020-10-02       Impact factor: 15.419

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