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Literature DB >> 26986819

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

Matthieu Jouffroy¹, Geraint H M Davies¹, Gary A Molander¹.

Abstract

A highly effective method for derivatizing 2,1-borazaronaphthalene cores using ammonium alkylbis(catecholato)silicates via photoredox/nickel dual catalysis is reported. By forging C(sp)(3)-C(sp)(2) bonds via this approach, alkyl fragments with various functional groups can be introduced to the azaborine core, affording previously inaccessible heterocyclic isosteres in good to excellent yields. The base-free, room-temperature conditions outlined allow sensitive functional group tolerance, even permitting the cross-coupling of unprotected primary and secondary amines.

Entities: Chemical Gene Species

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Year: 2016 PMID： 26986819 PMCID： PMC5373477 DOI： 10.1021/acs.orglett.6b00466

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

38 in total

1. Combining gold and photoredox catalysis: visible light-mediated oxy- and aminoarylation of alkenes.

Authors: Basudev Sahoo; Matthew N Hopkinson; Frank Glorius
Journal: J Am Chem Soc Date: 2013-04-08 Impact factor: 15.419

2. 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

3. BN/CC isosterism in borazaronaphthalenes towards phosphodiesterase 10A (PDE10A) inhibitors.

Authors: Alexandru Vlasceanu; Mikkel Jessing; John Paul Kilburn
Journal: Bioorg Med Chem Date: 2015-06-15 Impact factor: 3.641

4. 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

5. Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

Authors: Lingling Chu; Jeffrey M Lipshultz; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2015-05-26 Impact factor: 15.336

6. Benzazaborinines as Novel Bioisosteric Replacements of Naphthalene: Propranolol as an Example.

Authors: Frederik J R Rombouts; Fulgencio Tovar; Nigel Austin; Gary Tresadern; Andrés A Trabanco
Journal: J Med Chem Date: 2015-11-30 Impact factor: 7.446

7. Elemental isomerism: a boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands.

Authors: Hai-Bing Zhou; Kendall W Nettles; John B Bruning; Younchang Kim; Andrzej Joachimiak; Sanjay Sharma; Kathryn E Carlson; Fabio Stossi; Benita S Katzenellenbogen; Geoffrey L Greene; John A Katzenellenbogen
Journal: Chem Biol Date: 2007-06

8. Accessing 2-(hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: palladium-catalyzed cross-couplings of 2-(chloromethyl)-2,1-borazaronaphthalenes.

Authors: Gary A Molander; Javad Amani; Steven R Wisniewski
Journal: Org Lett Date: 2014-11-03 Impact factor: 6.005

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

Authors: Idris Karakaya; David N Primer; Gary A Molander
Journal: Org Lett Date: 2015-06-16 Impact factor: 6.005

10. Reductive cross-coupling of 3-bromo-2,1-borazaronaphthalenes with alkyl iodides.

Authors: Gary A Molander; Steven R Wisniewski; Kaitlin M Traister
Journal: Org Lett Date: 2014-06-30 Impact factor: 6.005

16 in total

1. Late-stage functionalization of BN-heterocycles.

Authors: Cameron R McConnell; Shih-Yuan Liu
Journal: Chem Soc Rev Date: 2019-07-01 Impact factor: 54.564

Review 2. The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications.

Authors: Zachary X Giustra; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2018-01-17 Impact factor: 15.419

3. 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

4. Medicinal Chemistry Profiling of Monocyclic 1,2-Azaborines.

Authors: Peng Zhao; David O Nettleton; Rajeshri G Karki; Frédéric J Zécri; Shih-Yuan Liu
Journal: ChemMedChem Date: 2017-02-21 Impact factor: 3.466

5. Preparation of Diisopropylammonium Bis(catecholato)cyclohexylsilicate.

Authors: Kingson Lin; Christopher B Kelly; Matthieu Jouffroy; Gary A Molander
Journal: Organic Synth Date: 2017

6. Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes.

Authors: Xie Wang; Geraint H M Davies; Adriel Koschitzky; Steven R Wisniewski; Christopher B Kelly; Gary A Molander
Journal: Org Lett Date: 2019-03-27 Impact factor: 6.005

7. Photoredox Catalysis in Organic Chemistry.

Authors: Megan H Shaw; Jack Twilton; David W C MacMillan
Journal: J Org Chem Date: 2016-08-01 Impact factor: 4.354

8. Selectivity in the Elaboration of Bicyclic Borazarenes.

Authors: Ayan Bhattacharjee; Geraint H M Davies; Borna Saeednia; Steven R Wisniewski; Gary A Molander
Journal: Adv Synth Catal Date: 2020-12-23 Impact factor: 5.837

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

Authors: Mark D Levin; Suhong Kim; F Dean Toste
Journal: ACS Cent Sci Date: 2016-05-03 Impact factor: 14.553

10. Single-Electron Transmetalation via Photoredox/Nickel Dual Catalysis: Unlocking a New Paradigm for sp(3)-sp(2) Cross-Coupling.

Authors: John C Tellis; Christopher B Kelly; David N Primer; Matthieu Jouffroy; Niki R Patel; Gary A Molander
Journal: Acc Chem Res Date: 2016-07-05 Impact factor: 22.384