Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones

2019 ◽  
Vol 17 (19) ◽  
pp. 4761-4766 ◽  
Author(s):  
Ruchi Chawla ◽  
Lal Dhar S. Yadav
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Cross Coupling ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Alkyl Aryl

Transition-metal- and oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from aryl diazonium and sulfinate salts employing eosin Y as an organo-photoredox catalyst is reported.

Visible light photoredox catalysis: conversion of a mixture of thiophenols and nitriles into 2-substituted benzothiazoles via consecutive C–S and C–N bond formation reactions

2018 ◽  
Vol 5 (9) ◽  
pp. 1527-1531 ◽  
Author(s):  
Palani Natarajan ◽  
Manjeet Manjeet ◽  
Muskan Muskan ◽  
Navpreet Kaur Brar ◽  
Jaskamal Jot Kaur
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Alkyl Aryl ◽  
Air Atmosphere ◽  
Aryl Nitriles ◽  
Bond Formation Reactions

A novel, visible-light-mediated method for the synthesis of 2-substituted benzothiazoles from thiophenols and alkyl/aryl nitriles in the presence of eosin Y under air atmosphere is disclosed.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Highly chemoselective deoxygenation of N-heterocyclic N-oxides under transition metal-free conditions

2021 ◽  
Vol 19 (16) ◽  
pp. 3735-3742
Author(s):  
Se Hyun Kim ◽  
Ju Hyeon An ◽  
Jun Hee Lee
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Eosin Y ◽  
Metal Free ◽  
Simple Protocol

Here, we provide an operationally simple protocol for the highly chemoselective deoxygenation of various functionalized N-heterocyclic N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst.

scholarly journals Copper’s rapid ascent in visible-light photoredox catalysis

Science ◽  
2019 ◽  
Vol 364 (6439) ◽  
pp. eaav9713 ◽  
Author(s):  
Asik Hossain ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Organic Dyes ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Photoredox Catalysis ◽  
Cross Coupling Reactions ◽  
Rapid Ascent ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.

8 Homogeneous visible light-mediated transition metal photoredox catalysis other than ruthenium and iridium

2013 ◽  
Author(s):  
Oliver Reiser ◽  
Georgiy Kachkovskyi ◽  
Viktor Kais ◽  
Paul Kohls ◽  
Suva Paria ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Photoredox Catalysis

Key Role of π–π Complex in Diary Cross-Coupling between Aryldiazonium Salts and Arylboronic Acids using Photosensitizer-Free Gold/Photoredox Catalysis

2021 ◽  
Author(s):  
Yanhong Liu ◽  
Rong-Xiu Zhu ◽  
Chengbu Liu ◽  
Dongju Zhang
Keyword(s):  
Dft Calculations ◽  
Visible Light ◽  
Cross Coupling ◽  
Photoredox Catalysis ◽  
Arylboronic Acids ◽  
Type Complex ◽  
Free Gold ◽  
Π Complex ◽  
Td Dft

DFT and TD-DFT calculations were performed to better understand the photosensitizer-free visible-light-mediated Au-catalyzed cross-couplings between aryldiazonium salts and arylboronic acids. The π–π type complex between the aryldiazonium salt and the...

Metal-free photocatalytic trifluoromethylative pyridylation of unactivated alkenes

2018 ◽  
Vol 20 (22) ◽  
pp. 5209-5214 ◽  
Author(s):  
Yu-Tao He ◽  
Dahye Kang ◽  
Inwon Kim ◽  
Sungwoo Hong
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Photoredox Catalysis ◽  
Metal Free

An efficient, transition metal-free trifluoromethylative pyridylation of unactivated alkenes was achieved by visible-light-induced photoredox catalysis.

scholarly journals C( sp 3 )−C( sp 3 ) Cross‐Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis

2020 ◽  
Vol 362 (12) ◽  
pp. 2367-2372 ◽  
Author(s):  
Marilia S. Santos ◽  
Arlene G. Corrêa ◽  
Márcio W. Paixão ◽  
Burkhard König
Keyword(s):  
Visible Light ◽  
Cross Coupling ◽  
Photoredox Catalysis ◽  
Alkyl Bromides

Synthesis of HIV NNRTI Doravirine Analogues via Visible-Light Photoredox Decarboxylative Cross-Coupling

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3177-3186
Author(s):  
Abdellatif ElMarrouni ◽  
Linda Suen ◽  
Cheng Wang ◽  
David Hunter ◽  
Helen Mitchell ◽  
...  
Keyword(s):  
Visible Light ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Parallel Synthesis ◽  
Photoredox Catalysis ◽  
Broad Applicability ◽  
Cross Coupling Reaction ◽  
Clinical Candidate

A C(sp2)–C(sp3) decarboxylative cross-coupling reaction utilizing dual nickel and photoredox catalysis for rapid parallel synthesis of diverse C-ring analogues of the HIV NNRTI clinical candidate doravirine is developed and described herein. This protocol features an alkylation with readily available and inexpensive methyl bromoacetate followed by hydrolysis to prepare an advanced doravirine intermediate, which undergoes decarboxylative cross-coupling with a variety of aryl and heteroaryl bromides. The mildness, broad applicability, and sustainability of the current methodology are improvements over previously reported procedures and allow for rapid parallel synthesis of analogues. The optimization and scope of this method are reported.

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