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Literature DB >> 26592731

α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Mirna El Khatib¹, Ricardo Augusto Massarico Serafim^1,2, Gary A Molander³.

Abstract

Direct access to complex, enantiopure benzylamine architectures using a synergistic iridium photoredox/nickel cross-coupling dual catalysis strategy has been developed. New C(sp(3))-C(sp(2)) bonds are forged starting from abundant and inexpensive natural amino acids.

Entities: Chemical Disease Gene

Keywords: amino acids; cross-coupling; heterocycles; nickel; photochemistry

Mesh：

Substances：

Year: 2015 PMID： 26592731 PMCID： PMC4795823 DOI： 10.1002/anie.201506147

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

34 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. Synthesis of α-amino acids based on chiral tricycloiminolactone derived from natural (+)-camphor.

Authors: Yong-Chun Luo; Huan-Huan Zhang; Yao Wang; Peng-Fei Xu
Journal: Acc Chem Res Date: 2010-10-19 Impact factor: 22.384

3. Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

Authors: Gary A Molander; Inji Shin
Journal: Org Lett Date: 2011-07-06 Impact factor: 6.005

4. Visible light photoredox catalysis: generation and addition of N-aryltetrahydroisoquinoline-derived α-amino radicals to Michael acceptors.

Authors: Paul Kohls; Deepak Jadhav; Ganesh Pandey; Oliver Reiser
Journal: Org Lett Date: 2012-01-19 Impact factor: 6.005

5. 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

6. 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

7. 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

8. Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions.

Authors: Shaoqun Zhu; Arindam Das; Lan Bui; Hanjun Zhou; Dennis P Curran; Magnus Rueping
Journal: J Am Chem Soc Date: 2013-01-18 Impact factor: 15.419

9. 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

10. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors: Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal: J Am Chem Soc Date: 2014-07-28 Impact factor: 15.419

25 in total

1. Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis.

Authors: Christopher B Kelly; Niki R Patel; David N Primer; Matthieu Jouffroy; John C Tellis; Gary A Molander
Journal: Nat Protoc Date: 2017-02-02 Impact factor: 13.491

2. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors: Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2018-01-04 Impact factor: 15.419

α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

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

2. Synthesis of α-amino acids based on chiral tricycloiminolactone derived from natural (+)-camphor.

3. Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

4. Visible light photoredox catalysis: generation and addition of N-aryltetrahydroisoquinoline-derived α-amino radicals to Michael acceptors.

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

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

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

8. Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions.

9. 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water.

10. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

1. Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis.

2. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

3. Accessing Elaborated 2,1-Borazaronaphthalene Cores Using Photoredox/Nickel Dual-Catalytic Functionalization.

4. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

5. Reactivity of (bi-Oxazoline)organonickel Complexes and Revision of a Catalytic Mechanism.

Review 6. Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.

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

8. Thioetherification via Photoredox/Nickel Dual Catalysis.

Review 9. Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling.

10. Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis.