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H Functionalization to Construct Heterocyclic Compounds Cite This: Chem ChemComm View Article Online FEATURE ARTICLE View Journal | View Issue Radical C–H functionalization to construct heterocyclic compounds Cite this: Chem. Commun., 2016, 52, 2220 Jin-Tao Yu*a and Changduo Pan*b Heterocyclic compounds are widely present in natural products, pharmaceuticals and bioactive molecules. Thus, organic and pharmaceutical chemists have been making extensive efforts to construct those heterocyclic frameworks through developing versatile and efficient synthetic strategies. The direct C–H functionalization via the radical pathway has emerged as a promising and dramatic approach Received 26th October 2015, towards heterocycles with high atom- and step-economy. Heterocyclic compounds such as coumarins, Accepted 17th December 2015 furans, benzofurans, xanthones, benzothiazoles, indoles, indolines, oxindoles, quinolines, isoquinolines, DOI: 10.1039/c5cc08872k quinoxaline, and phenanthridines have been successfully synthesized by C–H functionalization through the radical pathway. In this review, recent advances on radical C–H functionalization to construct hetero- www.rsc.org/chemcomm cyclic compounds are highlighted with discussions. 1. Introduction plastics are heterocyclic molecules. Therefore, organic chemists have been making extensive efforts to prepare these heterocyclic Heterocyclic compounds are widely spread in natural products compounds by developing new and efficient synthetic trans- and synthetic molecules and of immense important biologically formations. For quite a long history, transition-metal catalyzed as well as industrially. Their extreme importance is reflected synthesis occupied a particular part in the generation of hetero- in many aspects, while chief among them are their biological cyclic compounds.1 Modern radical reactions, which emerged in activities. The majority of pharmaceuticals and biologically the 1980s, have flourished recently. In light of the relatively mild active agrochemicals are heterocyclic compounds (take the reaction conditions and high atom economy, radical synthesis 2015 Nobel molecules Artemisinin and Abamectin, for examples). has become popular nowadays, and the radical cyclization Published on 17 December 2015. Downloaded 29/01/2016 01:29:40. Besides, countless additives and modifiers used in industries provides a new avenue in the synthesis of a great number of as varied as cosmetics, reprography, information storage and heterocyclic compounds, such as coumarins, furans, benzofurans, xanthones, benzothiazoles, indoles, indolines, oxindoles, quinolines, isoquinolines, quinoxaline, and phenanthridines. In recent years, a School of Petrochemical Engineering, Advanced Catalysis and Green direct C–H bond functionalization, which successfully avoids Manufacturing Collaborative Innovation Center, Changzhou University, the time and cost consuming prefunctionalizations, has been Changzhou 213164, P. R. China. E-mail: [email protected] b School of Chemistry & Environmental Engineering, Jiangsu University of recognized as a reliable method to construct complex molecules Technology, Changzhou 213001, P. R. China. E-mail: [email protected] due to high step- and atom-economy as well as the readily Dr Jin-Tao Yu was born in Dr Changduo Pan was born Shandong, China, in 1984. She in Zhejiang province, China. He received her PhD (2012) in Institute received his MS degree at Wenzhou of Chemistry Chinese Academy of University in the group of Prof. Jiang Sciences under the supervision of Cheng in 2009. After three years, he NA. Zhi-Tang Huang and Prof. Qi- joined Nanjing University under the Yu Zheng. From 2012, she works in supervision of Prof. Chengjian Zhu. Changzhou University. Her current He joined the Jiangsu University of research focuses on the transition- Technology in 2015. His current metal catalysis and radical C–H research mainly focuses on radical functionalization. chemistry. Jin-Tao Yu Changduo Pan 2220 | Chem. Commun., 2016, 52, 2220--2236 This journal is © The Royal Society of Chemistry 2016 View Article Online Feature Article ChemComm available starting materials.2 A great number of extinguishing studies have been accomplished by talented chemists all over the world. This review focuses on the recent advances in the construction of heterocyclic compounds by radical C–H functio- nalization with or without metal catalysts. The scope and limitations of these cyclization reactions are discussed, as well as their mechanisms. 2. Radical cyclization towards coumarins Scheme 2 The coumarin skeleton is a core structure that widely occurs in natural products, biological molecules and dyes.3 Traditional synthetic methods include the Pechmann reaction, Wittig reaction, vinyl radical 2. Then 2 undergoes cyclization to generate inter- and the Knoevenagel condensation. However, these protocols mediate 3. Subsequently, a single-electron transfer (SET) from 3 suffered from several drawbacks, such as inaccessible substrates to silver(I) releases the product along with HNO3 and silver(0). and catalysts, tedious performance, hazardous reagents, low Silver(0) could be oxidized to silver(I) by HNO3 to complete the atom economy and limited substrate scopes. Recently, direct catalytic cycle. difunctionalization of readily synthesized alkynoates has been Afterwards, Wu and other groups reported a series of radical utilized as an efficient route to access coumarins. difunctionalization reactions of alkynoates, including radical 9 Since aromatic organophosphorus compounds could be widely trifluoromethylation/cyclization with Togni’s reagent, aryldifluoro- 10 found in natural products, pharmaceuticals and materials,4 the acetylation/cyclization with ethyl bromodifluoroacetate, arylsul- 11 development of convenient C–P bond construction is crucial. fonylation/cyclization with arylsulfinic acids or sulfonyl hydrazides, P-centered radicals, which can be facilely generated from trifluoromethylthiolation and thiocyanation/cyclization with AgSCF3 12 13 common radical initiators such as peroxides,5 azo compounds,6 and AgSCN, acylation/cyclization with aldehydes and decar- 7 boxylation/cyclization with a-keto acids14 to synthesize various and Ag/K2S2O8, are reliable intermediates in the construction of organophosphorus compounds. Regarding this, Wu developed coumarin derivatives (Scheme 3). The reaction pathway is similar to the phosphorylation/cyclization of alkynoates,8 including (1) the Ag2CO3-catalyzed sequential radical C–P/C–C coupling process for the synthesis of 3-phosphorated coumarins utilizing dialkyl generation of carbon- or heteroatom-centered radicals via oxidation H-phosphonates as P-radical precursors (Scheme 1).8 Diverse of external oxidants or photocatalysts; (2) selectivity addition of Q dialkyl H-phosphonates as well as diphenylphosphine oxides certain radicals to the a-position of the C O bond in alkynoates are all suitable P-radical precursors to generate the desired to form the vinyl radical intermediate; (3) intramolecular radical Published on 17 December 2015. Downloaded 29/01/2016 01:29:40. products in moderate to good yields. The transformation is cyclization to form another radical intermediate with a six- sensitive to steric hindrance. No product was detected using the membered ring; (4) deprotonation and rearomatization to deliver substrate with a methyl group on the ortho-position of the the corresponding functionalized coumarin derivatives. phenoxy ring. The regioselectivity study using aryl alkynoates bearing a meta-substituted phenoxy ring showed that the cyclization preferably occurred at the position distal to the meta-substituent. It is worth noting that phenyl 2-octynoate is also a suitable reaction partner albeit in lower yield. The reaction could be completely suppressed by the addition of the radical scavenger TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy), which indicates the presence of a radical intermediate. Mechanism studies showed that the P-radicals are generated from dialkyl H-phosphonates oxidized by Ag2CO3 or from the in situ generated [R2P(O)Ag]. Accordingly, the radical cyclization mechanism is outlined in Scheme 2. Firstly, selectivity addition of the generated P-radical to the a-position of the CQO bond in alkynoates 1 gives Scheme 1 Scheme 3 This journal is © The Royal Society of Chemistry 2016 Chem. Commun., 2016, 52, 2220--2236 | 2221 View Article Online ChemComm Feature Article Scheme 4 Scheme 6 Very interestingly, Qiu revealed that the oxidative radical scopes and a host of benzoic acids could be transferred into their cyclization of alkynoates with a-keto acids resulted in the isomeric corresponding benzo-3,4-coumarins in good yields. In particular, structures rather than the above results when a catalytic amount of this procedure is mild enough to tolerate benzyl alcohols. Ag2CO3 was used together with 2.5 equivalents of NaOAc as an III 15 The reaction pathway is listed in Scheme 8. An active Cu additive (Scheme 4). Thus, Qiu deduced that the transformation intermediate 9 is involved in the catalytic procedure, which undergoes an unusual 5-exo annulation by the ester migration abstracts the adjacent H atom to form aryl radical 10 (Path A). pathway. As illustrated in Scheme 5, silver-catalyzed decarboxylation Upon oxidative ring closure 100 is produced, followed by a of 2-phenyl-2-oxoacetic acid gives acyl radical 4, which reacts reductive elimination to form coumarin products. Alternatively, with alkynoate 1 to generate intermediate 5. The following 5-exo a single-electron transfer (SET) process in 9 would give radical– cyclization
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