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Literature DB >> 29354317

Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Camille Remeur¹, Christopher B Kelly¹, Niki R Patel¹, Gary A Molander¹.

Abstract

A protocol for the aminomethylation of aryl halides using α-silylamines via Ni/photoredox dual catalysis is described. The low oxidation potential of these silylated species enables facile single electron transfer (SET) oxidation of the amine followed by rapid desilylation. The resulting α-amino radicals can be directly funneled into a nickel-mediated cross-coupling cycle with aryl halides. The process accomplishes aminomethylation under remarkably mild conditions and tolerates numerous aryl- and heteroaryl halides with an array of functional groups.

Entities: Chemical Gene Species

Keywords: aminomethylation; cross-coupling; nickel/photoredox dual catalysis; radicals; visible light

Year: 2017 PMID： 29354317 PMCID： PMC5771658 DOI： 10.1021/acscatal.7b01973

Source DB: PubMed Journal: ACS Catal Impact factor: 13.084

42 in total

1. Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors: Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal: Chem Rev Date: 2010-03-10 Impact factor: 60.622

2. Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides.

Authors: Aaron M Dumas; Adrian J Sieradzki; Liam J Donnelly
Journal: Org Lett Date: 2016-03-28 Impact factor: 6.005

3. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors: Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal: Science Date: 2014-06-05 Impact factor: 47.728

4. Potassium Boc-protected secondary aminomethyltrifluoroborates: synthesis and Suzuki-Miyaura cross-coupling reactions.

Authors: Gary A Molander; Inji Shin
Journal: Org Lett Date: 2012-08-29 Impact factor: 6.005

5. Synthesis, biological evaluation, and molecular modeling of donepezil and N-[(5-(benzyloxy)-1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine hybrids as new multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer's disease.

Authors: Irene Bolea; Jordi Juárez-Jiménez; Cristóbal de Los Ríos; Mourad Chioua; Ramón Pouplana; F Javier Luque; Mercedes Unzeta; José Marco-Contelles; Abdelouahid Samadi
Journal: J Med Chem Date: 2011-11-15 Impact factor: 7.446

6. Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

Authors: David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal: J Am Chem Soc Date: 2015-02-04 Impact factor: 15.419

7. 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water.

Authors: Wenyan Liao; Yunfeng Chen; Yuxiu Liu; Haifeng Duan; Jeffrey L Petersen; Xiaodong Shi
Journal: Chem Commun (Camb) Date: 2009-09-28 Impact factor: 6.222

Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

1. Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

2. Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides.

3. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

4. Potassium Boc-protected secondary aminomethyltrifluoroborates: synthesis and Suzuki-Miyaura cross-coupling reactions.

5. Synthesis, biological evaluation, and molecular modeling of donepezil and N-[(5-(benzyloxy)-1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine hybrids as new multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer's disease.

6. Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

7. 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water.

8. Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

9. Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers.

10. Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations.

1. Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source.

2. Late-Stage N-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis.

Review 3. Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.

4. Multifunctional Building Blocks Compatible with Photoredox-Mediated Alkylation for DNA-Encoded Library Synthesis.

5. Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics.

6. Developments in Photoredox-Mediated Alkylation for DNA-Encoded Libraries.

7. Accessing Aliphatic Amines in C-C Cross-Couplings by Visible Light/Nickel Dual Catalysis.

8. Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex.

9. A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions.