Trifluoromethanesulfonic Anhydride as a Low‐Cost and Versatile Trifluoromethylation Reagent DOI

Yao Ouyang,

Xiu‐Hua Xu, Feng‐Ling Qing

и другие.

Angewandte Chemie International Edition, Год журнала: 2018, Номер 57(23), С. 6926 - 6929

Опубликована: Апрель 19, 2018

Abstract A large number of reagents have been developed for the synthesis trifluoromethylated compounds. However, an ongoing challenge in trifluoromethylation reaction is use less expensive and practical trifluoromethyl sources. We report herein unprecedented direct (hetero)arenes using trifluoromethanesulfonic anhydride as a radical reagent by merging photoredox catalysis pyridine activation. Furthermore, introduction both CF 3 OTf groups into internal alkynes to access tetrasubstituted alkenes was achieved. Since low‐cost abundant chemical, this method provides cost‐efficient route

Язык: Английский

Radicals: Reactive Intermediates with Translational Potential DOI Creative Commons
Ming Yan,

Julian C. Lo,

Jacob T. Edwards

и другие.

Journal of the American Chemical Society, Год журнала: 2016, Номер 138(39), С. 12692 - 12714

Опубликована: Сен. 15, 2016

This Perspective illustrates the defining characteristics of free radical chemistry, beginning with its rich and storied history. Studies from our laboratory are discussed along recent developments emanating others in this burgeoning area. The practicality chemoselectivity reactions enable rapid access to molecules relevance drug discovery, agrochemistry, material science, other disciplines. Thus, these reactive intermediates possess inherent translational potential, as they can be widely used expedite scientific endeavors for betterment humankind.

Язык: Английский

Процитировано

905

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts DOI Creative Commons
Daniel Kaiser, Immo Klose,

Rik Oost

и другие.

Chemical Reviews, Год журнала: 2019, Номер 119(14), С. 8701 - 8780

Опубликована: Июнь 25, 2019

Organosulfur compounds have long played a vital role in organic chemistry and the development of novel chemical structures architectures. Prominent among these organosulfur are those involving sulfur(IV) center, which been subject countless investigations over more than hundred years. In addition to list textbook sulfur-based reactions, there has sustained interest organosulfur(IV) recent Of particular within is ease with synthetic chemist can effect wide range transformations through either bond formation or cleavage at sulfur. This review aims cover developments past decade molecules provide insight into both reactions critically rely on this versatile element diverse scaffolds that thereby be synthesized.

Язык: Английский

Процитировано

698

Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes DOI
Indrajit Ghosh, Jagadish Khamrai, Aleksandr Savateev

и другие.

Science, Год журнала: 2019, Номер 365(6451), С. 360 - 366

Опубликована: Июль 25, 2019

Two-for-one approach to photoredox In catalysis, an excited chromophore typically activates a single reactant either by oxidizing or reducing it. Ghosh et al. used semiconductor catalyst activate two reactants at once quenching both electron and the residual positive hole (see Perspective Swift). As such, different reactive carbon halide fragments could be appended separate sites on aryl ring. The also tolerated strong nucleophiles such as cyanide recovered easily reused. Science , this issue p. 360 ; see 320

Язык: Английский

Процитировано

513

C–H Functionalization of Azines DOI
Kei Murakami,

Shuya Yamada,

Takeshi Kaneda

и другие.

Chemical Reviews, Год журнала: 2017, Номер 117(13), С. 9302 - 9332

Опубликована: Апрель 26, 2017

Azines, which are six-membered aromatic compounds containing one or more nitrogen atoms, serve as ubiquitous structural cores of species with important applications in biological and materials sciences. Among a variety synthetic approaches toward azines, C-H functionalization represents the most rapid atom-economical transformation, it is advantageous for late-stage azine-containing functional molecules. Since azines have several bonds different reactivities, development new reactions that allow regioselective fashion has comprised central issue. This review describes recent advances categorized follows: (1) SNAr reactions, (2) radical (3) deprotonation/functionalization, (4) metal-catalyzed reactions.

Язык: Английский

Процитировано

469

A General Small-Scale Reactor To Enable Standardization and Acceleration of Photocatalytic Reactions DOI Creative Commons
Chi “Chip” Le,

Michael K. Wismer,

Zhi-Cai Shi

и другие.

ACS Central Science, Год журнала: 2017, Номер 3(6), С. 647 - 653

Опубликована: Май 17, 2017

Photocatalysis for organic synthesis has experienced an exponential growth in the past 10 years. However, variety of experimental procedures that have been reported to perform photon-based catalyst excitation hampered establishment general protocols convert visible light into chemical energy. To address this issue, we designed integrated photoreactor enhanced photon capture and excitation. Moreover, evaluation new reactor eight photocatalytic transformations are widely employed medicinal chemistry settings confirmed significant performance advantages optimized design while enabling a standardized protocol.

Язык: Английский

Процитировано

223

Aryl Sulfonium Salts for Site‐Selective Late‐Stage Trifluoromethylation DOI Creative Commons
Fei Ye, Florian Berger, Hao Jia

и другие.

Angewandte Chemie International Edition, Год журнала: 2019, Номер 58(41), С. 14615 - 14619

Опубликована: Авг. 7, 2019

Abstract Incorporation of the CF 3 group into arenes has found increasing importance in drug discovery. Herein, we report first photoredox‐catalyzed cross‐coupling aryl thianthrenium salts with a copper‐based trifluoromethyl reagent, which enables site‐selective late‐stage trifluoromethylation arenes. The reaction proceeds broad functional tolerance, even for complex small molecules on gram scale. method was further extended to produce pentafluoroethylated derivatives.

Язык: Английский

Процитировано

219

Perspectives on green synthesis and catalysis DOI Creative Commons

Yiram Kim,

Chao‐Jun Li

Green Synthesis and Catalysis, Год журнала: 2020, Номер 1(1), С. 1 - 11

Опубликована: Июнь 1, 2020

Despite their impressive capacity to access diverse functional groups and synthesize structurally complex molecules, the majority of organic reactions suffers from harsh conditions, low atom economy, hazardous waste production. The goal our research is geared towards developing efficient methods minimize adverse environmental impact contributing chemical sustainability. Herein, we illustrate three distinct green approaches, studying novel reactivities with environmentally innocuous reagents improve synthetic efficiency, utilization natural feedstocks, employment energy facilitate various important transformations. From this perspective article, hope provide an overview chemistry inspire expansion field in future.

Язык: Английский

Процитировано

203

Photochemical and Electrochemical Carbon Dioxide Utilization with Organic Compounds DOI
Yu Cao, Xing He,

Ning Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2018, Номер 36(7), С. 644 - 659

Опубликована: Апрель 17, 2018

Abstract In the last few years, photochemical and electrochemical CO 2 transformations have attracted increasing attention in response to topical interest renewable energy green chemistry. The present minireview offers an overview about current approaches for carbon dioxide fixation with organic compounds. Valuable products, including carboxylic acids heterocyclic compounds, are accessible through carboxylation carboxylative cyclization, respectively. processes, photo‐ or electro‐induced radical ions other high‐energy compounds considered as key intermediates react . Besides, activation of produce anion has also been reported.

Язык: Английский

Процитировано

196

Fluoroalkylation reactions in aqueous media: a review DOI

Hai‐Xia Song,

Qiu‐Yan Han,

Chenglong Zhao

и другие.

Green Chemistry, Год журнала: 2018, Номер 20(8), С. 1662 - 1731

Опубликована: Янв. 1, 2018

Recent advances in aqueous fluoroalkylation using various reagents are summarized this review.

Язык: Английский

Процитировано

186

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH DOI Creative Commons
Wenbo Liu, Xiaobo Yang, Zhong‐Zhen Zhou

и другие.

Chem, Год журнала: 2017, Номер 2(5), С. 688 - 702

Опубликована: Май 1, 2017

Язык: Английский

Процитировано

182