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Literature DB >> 26959863

Boron-Catalyzed Aromatic C-H Bond Silylation with Hydrosilanes.

Yuanhong Ma¹, Baoli Wang¹, Liang Zhang¹, Zhaomin Hou¹.

Abstract

Metal-free catalytic C-H silylation of a series of aromatic compounds such as N,N-disubstituted anilines with various hydrosilanes has been achieved for the first time using commercially available B(C6F5)3 as a catalyst. This protocol features simple and neutral reaction conditions, high regioselectivity, wide substrate scope (up to 40 examples), Si-Cl bond compatibility, and no requirement for a hydrogen acceptor.

Entities: Chemical

Year: 2016 PMID： 26959863 DOI： 10.1021/jacs.6b01349

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

14 in total

1. Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds.

Authors: Bo Su; John F Hartwig
Journal: J Am Chem Soc Date: 2017-08-25 Impact factor: 15.419

Review 2. Activation of Si-H and B-H bonds by Lewis acidic transition metals and p-block elements: same, but different.

Authors: Pablo Ríos; Amor Rodríguez; Salvador Conejero
Journal: Chem Sci Date: 2022-06-06 Impact factor: 9.969

3. Iridium-Catalyzed, β-Selective C(sp³)-H Silylation of Aliphatic Amines To Form Silapyrrolidines and 1,2-Amino Alcohols.

Authors: Bo Su; Taegyo Lee; John F Hartwig
Journal: J Am Chem Soc Date: 2018-12-13 Impact factor: 15.419

4. A well-defined NHC-Ir(iii) catalyst for the silylation of aromatic C-H bonds: substrate survey and mechanistic insights.

Authors: Laura Rubio-Pérez; Manuel Iglesias; Julen Munárriz; Victor Polo; Vincenzo Passarelli; Jesús J Pérez-Torrente; Luis A Oro
Journal: Chem Sci Date: 2017-04-05 Impact factor: 9.825

10. An effective and versatile strategy for the synthesis of structurally diverse heteroarylsilanes via Ir(iii)-catalyzed C-H silylation.

Authors: Zhi-Bo Yan; Meng Peng; Qi-Long Chen; Ka Lu; Yong-Qiang Tu; Kun-Long Dai; Fu-Min Zhang; Xiao-Ming Zhang
Journal: Chem Sci Date: 2021-06-08 Impact factor: 9.825

Boron-Catalyzed Aromatic C-H Bond Silylation with Hydrosilanes.

1. Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds.

Review 2. Activation of Si-H and B-H bonds by Lewis acidic transition metals and p-block elements: same, but different.

3. Iridium-Catalyzed, β-Selective C(sp³)-H Silylation of Aliphatic Amines To Form Silapyrrolidines and 1,2-Amino Alcohols.

4. A well-defined NHC-Ir(iii) catalyst for the silylation of aromatic C-H bonds: substrate survey and mechanistic insights.

5. para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis.

6. Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes.

7. Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel-Crafts reaction.

8. Consecutive β,β'-Selective C(sp³ )-H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C₆ F₅ )₃.

9. B(C₆F₅)₃-Catalyzed C-C Coupling of 1,4-Naphthoquinones with the C-3 Position of Indole Derivatives in Water.

10. An effective and versatile strategy for the synthesis of structurally diverse heteroarylsilanes via Ir(iii)-catalyzed C-H silylation.