Visible Light‐Induced Photocatalytic C−H Perfluoroalkylation of Quinoxalinones under Aerobic Oxidation Condition DOI

Zhenjiang Wei,

Sijia Qi,

Yanhao Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(23), P. 5490 - 5498

Published: Sept. 16, 2019

Abstract An efficient approach using a photocatalytic strategy for C−H perfluoroalkylation of quinoxalinones under aerobic oxidation condition has been developed. Such transformation employs readily available sodium perfluoroalkanesulfinates as reagents and demonstrates good functional group compatibility, affording corresponding products in moderate to yields. Compared with previous procedures, this protocol uses oxygen oxidant, avoids the use external additive. A radical mechanism is involved reaction. magnified image

Language: Английский

Photoredox-Catalyzed C–H Functionalization Reactions DOI

Natalie Holmberg‐Douglas,

David A. Nicewicz

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1925 - 2016

Published: Sept. 29, 2021

The fields of C–H functionalization and photoredox catalysis have garnered enormous interest utility in the past several decades. Many different scientific disciplines relied on strategies including natural product synthesis, drug discovery, radiolabeling, bioconjugation, materials, fine chemical synthesis. In this Review, we highlight use reactions. We separate review into inorganic/organometallic catalysts organic-based catalytic systems. Further subdivision by reaction class─either sp2 or sp3 functionalization─lends perspective tactical for these methods synthetic applications.

Language: Английский

Citations

651

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis DOI Creative Commons
Philip R. D. Murray, James H. Cox, Nicholas D. Chiappini

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2017 - 2291

Published: Nov. 23, 2021

We present here a review of the photochemical and electrochemical applications multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms which both an proton exchanged together, often concerted elementary step. As such, MS-PCET can function as non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from wide variety common functional groups. introduction practitioner’s guide reaction design, with emphasis on unique energetic selectivity features that characteristic this class. then chapters oxidative N–H, O–H, S–H, C–H homolysis methods, generation corresponding neutral species. Then, reductive PCET activations involving carbonyl, imine, other X═Y π-systems, heteroarenes, where ketyl, α-amino, heteroarene-derived radicals be generated. Finally, we asymmetric catalysis materials device applications. Within each chapter, subdivide by group undergoing homolysis, thereafter type transformation being promoted. Methods published prior end December 2020 presented.

Language: Английский

Citations

358

Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis DOI
Kitae Kwon,

R. Thomas Simons,

Meganathan Nandakumar

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2353 - 2428

Published: Oct. 8, 2021

For more than 70 years, nitrogen-centered radicals have been recognized as potent synthetic intermediates. This review is a survey designed for use by chemists engaged in target-oriented synthesis. summarizes the recent paradigm shift access to and application of N-centered enabled visible-light photocatalysis. broadens streamlines approaches many small molecules because photocatalysis conditions are mild. Explicit attention paid innovative advances N–X bonds radical precursors, where X = Cl, N, S, O, H. clarity, key mechanistic data noted, available. Synthetic applications limitations summarized illuminate tremendous utility photocatalytically generated radicals.

Language: Английский

Citations

269

Visible light promoted cross-dehydrogenative coupling: a decade update DOI
Avik Kumar Bagdi, Matiur Rahman, Dhananjay Bhattacherjee

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(20), P. 6632 - 6681

Published: Jan. 1, 2020

In this review, all the visible light promoted cross-dehydrogenative coupling methodologies that have been developed over last decade are disclosed.

Language: Английский

Citations

197

Recent advances in the direct functionalization of quinoxalin-2(1H)-ones DOI

Qiumin Ke,

Guobing Yan, Jian Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(24), P. 5863 - 5881

Published: Jan. 1, 2019

The direct C3-functionalization of quinoxalin-2(1H)-ones via C–H bond activation has recently attracted considerable attention, due to their diverse biological activities and chemical properties.

Language: Английский

Citations

189

Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids under metal-, strong oxidant- and external photocatalyst-free conditions DOI
Long‐Yong Xie,

You-Shu Bai,

Xiang-Qin Xu

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(5), P. 1720 - 1725

Published: Jan. 1, 2020

An eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones and α-oxo carboxylic acids with air as the oxidant under external-photocatalyst-free conditions was established.

Language: Английский

Citations

174

Recent advances in visible-light-mediated organic transformations in water DOI
Kai Sun, Qi‐Yan Lv, Xiaolan Chen

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 23(1), P. 232 - 248

Published: Dec. 11, 2020

Water is a green reaction medium, while visible light represents renewable, clean, and abundant energy source. The recent advances in visible-light-mediated organic transformations water are summarized.

Language: Английский

Citations

161

Catalyst-free visible-light-initiated oxidative coupling of aryldiazo sulfones with thiols leading to unsymmetrical sulfoxides in air DOI
Qishun Liu, Leilei Wang, Huilan Yue

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(7), P. 1609 - 1613

Published: Jan. 1, 2019

A facile visible-light-driven method has been developed to construct sulfoxides from aryldiazo sulfones and thiols in air under photocatalyst-free conditions.

Language: Английский

Citations

149

Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones DOI
Kai Sun, Fang Xiao, Bing Yu

et al.

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2021, Volume and Issue: 42(11), P. 1921 - 1943

Published: Aug. 30, 2021

Language: Английский

Citations

138

Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones DOI
Zhiwei Wang, Qishun Liu,

Ruisheng Liu

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(3), P. 1479 - 1482

Published: Aug. 12, 2021

Language: Английский

Citations

134