Literature DB >> 32491868

Germylation of Arenes via Pd(I) Dimer Enabled Sulfonium Salt Functionalization.

Aymane Selmani1, Avetik G Gevondian1, Franziska Schoenebeck1.   

Abstract

While aryl germanes have recently found usage as coupling partners in powerful catalytic applications, the synthetic access to this promising functionality is currently limited. This report details the straightforward synthesis of functionalized aryl triethylgermanes via formal C-H functionalization. Building on the concept of directing-group-free and site-selective C-H functionalization of arenes to thianthrenium salt intermediates, we showcase their efficient couplings with triethylgermane (Et3Ge-H) at room temperature, which was enabled by the air- and moisture-stable Pd(I) dimer, [Pd(μ-I)(PtBu3)]2. The method tolerates numerous functional groups, including valuable (pseudo)halides.

Entities:  

Year:  2020        PMID: 32491868     DOI: 10.1021/acs.orglett.0c01609

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

Review 1.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

Authors:  Bogdan Marciniec; Cezary Pietraszuk; Piotr Pawluć; Hieronim Maciejewski
Journal:  Chem Rev       Date:  2021-12-30       Impact factor: 60.622

2.  Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts.

Authors:  María Jesús Cabrera-Afonso; Albert Granados; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-30       Impact factor: 16.823

3.  Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF3+, CF3, and CF3- Reactivity.

Authors:  Hao Jia; Andreas P Häring; Florian Berger; Li Zhang; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2021-05-14       Impact factor: 15.419

Review 4.  Late stage C-H functionalization via chalcogen and pnictogen salts.

Authors:  Christopher B Kelly; Rosaura Padilla-Salinas
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

5.  Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene.

Authors:  Fabio Juliá; Jiyao Yan; Fritz Paulus; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2021-08-10       Impact factor: 15.419

6.  High Site Selectivity in Electrophilic Aromatic Substitutions: Mechanism of C-H Thianthrenation.

Authors:  Fabio Juliá; Qianzhen Shao; Meng Duan; Matthew B Plutschack; Florian Berger; Javier Mateos; Chenxi Lu; Xiao-Song Xue; K N Houk; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2021-09-21       Impact factor: 15.419

7.  A Perspective on Late-Stage Aromatic C-H Bond Functionalization.

Authors:  Li Zhang; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2022-01-27       Impact factor: 15.419

8.  Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group.

Authors:  Tatjana Kreisel; Marvin Mendel; Adele E Queen; Kristina Deckers; Daniel Hupperich; Julian Riegger; Christoph Fricke; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-21       Impact factor: 16.823

9.  Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations.

Authors:  Christoph Fricke; Kristina Deckers; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-20       Impact factor: 16.823

  9 in total

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