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Literature DB >> 24445986

Catalytic metal-free Si-N cross-dehydrocoupling.

Abstract

The metal-free B(C6F5)3 catalyzed dehydrocoupling of hydrosilanes with anilines, carbazoles and indoles is reported. For anilines and carbazoles the reaction proceeds by the liberation of H2 as the sole Si-N coupling byproduct. Indoles react with diphenyl(methyl) hydrosilane to give N-silyl indolines with high diastereoselectivity (d.r. 10 : 1) in excellent yields. A mechanism for this Si-N coupling/hydrogenation sequence is proposed.

Entities: Chemical Gene

Year: 2014 PMID： 24445986 DOI： 10.1039/c3cc49558b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

7 in total

Review 1. 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

2. Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.

Authors: Manuel Pérez; Christopher B Caputo; Roman Dobrovetsky; Douglas W Stephan
Journal: Proc Natl Acad Sci U S A Date: 2014-07-07 Impact factor: 11.205

3. B(C₆F₅)₃-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation.

Authors: Murali Mohan Guru; Sriman De; Sayan Dutta; Debasis Koley; Biplab Maji
Journal: Chem Sci Date: 2019-07-05 Impact factor: 9.825

4. Comparative DFT study of metal-free Lewis acid-catalyzed C-H and N-H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope.

Authors: Pan Du; Jiyang Zhao
Journal: RSC Adv Date: 2019-11-19 Impact factor: 3.361

Catalytic metal-free Si-N cross-dehydrocoupling.

Review 1. Activation of Si-H and B-H bonds by Lewis acidic transition metals and p-block elements: same, but different.

2. Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.

3. B(C₆F₅)₃-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation.

4. Comparative DFT study of metal-free Lewis acid-catalyzed C-H and N-H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope.

5. Introducing the Catalytic Amination of Silanes via Nitrene Insertion.

6. FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers.

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

Catalytic metal-free Si-N cross-dehydrocoupling.

Review 1. Activation of Si-H and B-H bonds by Lewis acidic transition metals and p-block elements: same, but different.

2. Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis.

3. B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation.

4. Comparative DFT study of metal-free Lewis acid-catalyzed C-H and N-H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope.

5. Introducing the Catalytic Amination of Silanes via Nitrene Insertion.

6. FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers.

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

3. B(C₆F₅)₃-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation.

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