Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation

Science ◽  
2018 ◽  
Vol 361 (6409) ◽  
pp. 1369-1373 ◽  
Author(s):  
Timothy M. Monos ◽  
Rory C. McAtee ◽  
Corey R. J. Stephenson
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Bond Formation ◽  
Single Electron ◽  
Convergent Synthesis ◽  
Alkene Oxidation ◽  
Synthetic Strategy ◽  
Nitrogen Bond

Alkene aminoarylation with a single, bifunctional reagent is a concise synthetic strategy. We report a catalytic protocol for the addition of arylsulfonylacetamides across electron-rich alkenes with complete anti-Markovnikov regioselectivity and excellent diastereoselectivity to provide 2,2-diarylethylamines. In this process, single-electron alkene oxidation enables carbon-nitrogen bond formation to provide a key benzylic radical poised for a Smiles-Truce 1,5-aryl shift. This reaction is redox-neutral, exhibits broad functional group compatibility, and occurs at room temperature with loss of sulfur dioxide. As this process is driven by visible light, uses readily available starting materials, and demonstrates convergent synthesis, it is well suited for use in a variety of synthetic endeavors.

A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide

2020 ◽  
Vol 22 (6) ◽  
pp. 1906-1910 ◽  
Author(s):  
Xinxing Gong ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Xiaona Fan ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature.

ChemInform Abstract: Room Temperature C-P Bond Formation Enabled by Merging Nickel Catalysis and Visible-Light-Induced Photoredox Catalysis.

ChemInform ◽  
2015 ◽  
Vol 46 (32) ◽  
pp. no-no
Author(s):  
Jun Xuan ◽  
Ting-Ting Zeng ◽  
Jia-Rong Chen ◽  
Liang-Qiu Lu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Nickel Catalysis ◽  
Photoredox Catalysis

Recent Advances in Nitrogen–Nitrogen Bond Formation

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 3835-3847 ◽  
Author(s):  
Qihang Guo ◽  
Zhan Lu
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Pyrazole Derivatives ◽  
Triazole Derivatives ◽  
Synthetic Strategy ◽  
Recent Advances ◽  
Intermolecular Reactions ◽  
Nitrogen Bond

Over the last decade, N–N bond formation as a synthetic strategy has emerged as a powerful key step in the construction of highly valuable heterocycles from easily obtained materials. This review focuses on recent methods used to build N–N bonds, classified by intra- and intermolecular reactions with various types of N–X (O, C, N, H) bond cleavage.1 I ntroduction2 Intramolecular N–N Bond Formation2.1 Cleavage of N–O Bonds2.2 Cleavage of N–C Bonds2.3 Cleavage of N–N Bonds2.4 Cleavage of N–H Bonds2.4.1 Construction of Pyrazole Derivatives2.4.2 Construction of Triazole Derivatives2.4.3 Construction of Indazole and Pyrazoline Derivatives2.4.4 Construction of Other N–N Bond Derivatives3 Intermolecular N–N Bond Formation4 Conclusion

Room Temperature CP Bond Formation Enabled by Merging Nickel Catalysis and Visible-Light-Induced Photoredox Catalysis

2015 ◽  
Vol 21 (13) ◽  
pp. 4962-4965 ◽  
Author(s):  
Jun Xuan ◽  
Ting-Ting Zeng ◽  
Jia-Rong Chen ◽  
Liang-Qiu Lu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Nickel Catalysis ◽  
Photoredox Catalysis

scholarly journals Catalytic Asymmetric Allylation of Aldehydes with Alkenes Mediated by Organophotoredox and Chiral Chromium Hybrid Catalysis

2018 ◽  
Author(s):  
Harunobu Mitsunuma ◽  
Shun Tanabe ◽  
Hiromu Fuse ◽  
Kei Ohkubo ◽  
Motomu Kanai
Keyword(s):  
Visible Light ◽  
Hybrid System ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Functional Group ◽  
Light Irradiation ◽  
Asymmetric Allylation ◽  
Complex Catalyst ◽  
Homoallylic Alcohols ◽  
Catalytic Asymmetric

A hybrid system accomplishing cooperativity between an organophotoredox acridinium catalyst and a chiral chromium<br>complex catalyst was developed, enabling the unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for the asymmetric allylation of aldehydes. The reaction proceeded under visible light irradiation at room temperature and with high functional group tolerance, affording the corresponding homoallylic alcohols with up to >20/1 diastereomeric ratio and 99% ee. The addition of Mg(ClO4)2 elicited profound enhancement of both reactivity and enantioselectivity.

Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes

2021 ◽  
Vol 8 (1) ◽  
pp. 94-100
Author(s):  
Jiaxin Liu ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Visible Light ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Synthetic Strategy ◽  
Rapid Construction

A new synthetic strategy of a single-electron oxidation and MHAT of methylenecyclopropanes (MCPs) for the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives by merging photoredox catalysis and cobalt catalysis has been developed.

scholarly journals Recent application of visible-light induced radicals in C–S bond formation

RSC Advances ◽  
2020 ◽  
Vol 10 (34) ◽  
pp. 20046-20056 ◽  
Author(s):  
Vishal Srivastava ◽  
Pravin K. Singh ◽  
Arjita Srivastava ◽  
Praveen P. Singh
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Organic Compounds ◽  
High Efficiency ◽  
Bond Formation ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Recent Application

The sulphur centered radicals, produced from various organic compounds, in high efficiency by single-electron-transfer (SET) oxidation.

Anionic Cyclometallated platinum(II) Tetrazolato Complexes as Viable Photoredox Catalysts

2018 ◽  
Author(s):  
Anna Maria Ranieri ◽  
Liam Burt ◽  
Stefano Stagni ◽  
Stefano Zacchini ◽  
Brian Skelton ◽  
...  
Keyword(s):  
Solid State ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Photophysical Properties ◽  
General Structure ◽  
No Emission ◽  
Michael Acceptors ◽  
Catalyzed Reactions

The synthesis, characterization, photophysical and photocatalytic studies of anionic platinum(II) tetrazolato complexes, with the general structure [TBA][Pt(CNC)TzR], are reported, where CNC<sup>2-</sup>represents a doubly cyclometalated 2,4,6-triphenylpyridine, TzR<sup>- </sup>is an anionic 5-substituted tetrazolato ligand (with a variable R functional group) and TBA<sup>+ </sup>is the tetrabutylammonium countercation. The complexes were prepared by substitution of the DMSO ligand in [Pt(CNC)(DMSO)] with the corresponding tetrazolato ligand. No emission from the platinum(II) complexes was detected at room temperature in solution, but the photophysical properties could be assessed in the solid state, where all the complexes display emission bands attributed to aggregates. The platinum(II) complexes were found to facilitate a range of fundamental classes of visible-light-mediated photoredox-catalyzed reactions, including α‑amino C–H functionalization processes, such as Povarov-type reactions and the addition of α-amino C–H bonds across Michael acceptors, in addition to ATRA chemistry, and a hydrodeiodination. With the exception of the hydrodeiodination process, the best Pt(II) catalysts provided turnover numbers of 150–175 in each of these transformations.

Visible-light mediated sulfonylation of thiols via insertion of sulfur dioxide

2019 ◽  
Vol 17 (24) ◽  
pp. 5897-5901 ◽  
Author(s):  
Akshay M. Nair ◽  
Shreemoyee Kumar ◽  
Indranil Halder ◽  
Chandra M. R. Volla
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Room Temperature

Photocatalytically generated sulfenyl radicals were coupled with arylsulfonyl radicals at room temperature for accessing unsymmetrical organic thiosulfonates.

Oxidative organophotoredox catalysis: a regioselective synthesis of 2-nitro substituted imidazopyridines and 3-substituted indoles, initiated by visible light

2016 ◽  
Vol 40 (11) ◽  
pp. 9694-9701 ◽  
Author(s):  
Snehlata Yadav ◽  
Madhulika Srivastava ◽  
Pratibha Rai ◽  
Bhartendu Pati Tripathi ◽  
Anu Mishra ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Bond Formation ◽  
Light Irradiation ◽  
Regioselective Synthesis ◽  
Metal Free

Intramolecular C–N heterocyclization and C–C bond formation under visible light irradiation at room temperature was accomplished with a metal-free photoredox catalyst.

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