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Additive free, N-heterocyclic nitrenium catalyzed photoreduction of cycloketone oxime esters† 无添加剂，n -杂环氮催化光还原环酮肟酯†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01961b
Xiao-Di Su , Zhu-Sheng Yang , Wei Gong , Zhi-Xiang Wang , Xiang-Yu Chen
{"title":"Additive free, N-heterocyclic nitrenium catalyzed photoreduction of cycloketone oxime esters†","authors":"Xiao-Di Su , Zhu-Sheng Yang , Wei Gong , Zhi-Xiang Wang , Xiang-Yu Chen","doi":"10.1039/d2qo01961b","DOIUrl":"10.1039/d2qo01961b","url":null,"abstract":"We report that N-heterocyclic nitreniums (NHNs) can be used as ideal charge transfer complex catalysts in the absence of any additives for the photoactivation of cycloketone oxime esters, where the...","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 5","pages":"Pages 1160-1165"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934858","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
An extended quinoid molecule based on bis(thiophene-diketopyrrolopyrrole) with balanced ambipolar semiconducting properties and strong near-infrared absorption† 基于双噻吩-二酮吡咯-吡咯的扩展类醌分子，具有平衡的双极性半导体性质和强近红外吸收†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01678h
Wansong Shang , Guangchao Han , Qingrui Fan , Xiaobo Yu , Dongsheng Liu , Cheng Li , Xi-Sha Zhang , Yuanping Yi , Guanxin Zhang , Deqing Zhang
{"title":"An extended quinoid molecule based on bis(thiophene-diketopyrrolopyrrole) with balanced ambipolar semiconducting properties and strong near-infrared absorption†","authors":"Wansong Shang ,&nbsp;Guangchao Han ,&nbsp;Qingrui Fan ,&nbsp;Xiaobo Yu ,&nbsp;Dongsheng Liu ,&nbsp;Cheng Li ,&nbsp;Xi-Sha Zhang ,&nbsp;Yuanping Yi ,&nbsp;Guanxin Zhang ,&nbsp;Deqing Zhang","doi":"10.1039/d2qo01678h","DOIUrl":"10.1039/d2qo01678h","url":null,"abstract":"<div><p>Organic semiconductors that exhibit strong absorption in the near-infrared (NIR) region have received increasing attention as new organic optoelectronic materials. In this paper, we report the synthesis, absorption and semiconducting properties of a new quinoid molecule based on bis(thiophene-diketopyrrolopyrrole) (2DPP-Q-CN) with a long conjugation length. The results reveal that this new quinoid molecule shows strong absorption in the NIR region with a molar extinction coefficient of 380 000 M<sup>−1</sup> cm<sup>−1</sup>. Moreover, the thin film of 2DPP-Q-CN exhibits balanced ambipolar semiconducting properties with hole and electron mobilities up to 0.19 and 0.20 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>, respectively.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 3","pages":"Pages 632-639"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3934908","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ru(ii)-catalyzed C–H alkynylation of ferrocenes with bromoalkynes directed by carboxamide groups† Ru（ii）催化的二茂铁与溴炔烃的C–H炔化反应，由羧酰胺基团指导†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00069a
Ru-Yuan Zhao , Jing Zhang , Rui-Han Niu , Jin-Heng Li , Bo Sun
{"title":"Ru(ii)-catalyzed C–H alkynylation of ferrocenes with bromoalkynes directed by carboxamide groups†","authors":"Ru-Yuan Zhao ,&nbsp;Jing Zhang ,&nbsp;Rui-Han Niu ,&nbsp;Jin-Heng Li ,&nbsp;Bo Sun","doi":"10.1039/d3qo00069a","DOIUrl":"10.1039/d3qo00069a","url":null,"abstract":"<div><p>An efficient synthesis of ferrocene derivatives <em>via</em> Ru(<span>ii</span>)-catalyzed direct selective C–H mono-alkynylation with easily accessible bromoalkyne compounds under the influence of weakly coordinating amide groups has been presented. This protocol provides an approach for accessing various ferrocene derivatives with easily transformed alkynes using carboxamides, giving alkynylated ferrocenes in up to 89% yield.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 8","pages":"Pages 2007-2012"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3856236","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Substrate-controlled divergent synthesis with ortho-vinyl-functionalised 1,3-enynes and imines via palladium catalysis† 钯催化邻乙烯基官能化1,3-烯和亚胺的底物控制发散合成†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00714f
Bo Zhu , Teng Sun , Zhi-Chao Chen , Lu Gao , Wei Du , Ying-Chun Chen
{"title":"Substrate-controlled divergent synthesis with ortho-vinyl-functionalised 1,3-enynes and imines via palladium catalysis†","authors":"Bo Zhu ,&nbsp;Teng Sun ,&nbsp;Zhi-Chao Chen ,&nbsp;Lu Gao ,&nbsp;Wei Du ,&nbsp;Ying-Chun Chen","doi":"10.1039/d3qo00714f","DOIUrl":"10.1039/d3qo00714f","url":null,"abstract":"<div><p>Presented herein is a substrate-controlled diversity-oriented approach to access skeletally different frameworks from <em>ortho</em>-vinyl-functionalised 1,3-enynes and imines <em>via</em> palladium catalysis. A variety of benzofulvenes were constructed in moderate to high yields, enantioselectivity and <em>E</em>-selectivity, through a cascade vinylogous addition, <em>5-exo-trig</em> migratory insertion and β-H elimination process. In addition, modifing the vinyl substitutions of 1,3-enyne substrates could switch the Oppolzer cyclisation into a <em>6-endo-trig</em> pattern, which finally furnished formal 1-naphthylated amines enantioselectively under similar conditions. Moreover, the 2-furyl imine-derived naphthalene products further underwent a domino intramolecular Diels–Alder cycloaddition reaction, furnishing complex oxabicyclo[2.2.1]heptane architectures. The efficient construction of distinctly structured libraries exhibited well the versatility of the current substrate-controlled strategy.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 13","pages":"Pages 3300-3306"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3856258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis† Au/N-杂环卡宾中继催化下通过环异构化/[4+3]环化过程不对称合成螺呋并[2,3-b]氮杂平-5,3′-吲哚啉衍生物†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00539a
Mengwei You , Yan Li , Xin Lv , Guodong Shen , Xiao Xiao , Liejin Zhou
{"title":"Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivatives via cycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis†","authors":"Mengwei You ,&nbsp;Yan Li ,&nbsp;Xin Lv ,&nbsp;Guodong Shen ,&nbsp;Xiao Xiao ,&nbsp;Liejin Zhou","doi":"10.1039/d3qo00539a","DOIUrl":"10.1039/d3qo00539a","url":null,"abstract":"<div><p>A variety of enantioenriched spirofuro[2,3-<em>b</em>]azepine-5,3′-indoline derivatives (dr &gt; 20 : 1, up to 96% ee) were facilely synthesized through cycloisomerization/asymmetric formal [4 + 3] cycloaddition reactions of enyne-amides with isatin-derived enals under gold(<span>i</span>)/chiral N-heterocyclic carbene (NHC) relay catalysis. The method is practical and useful because of the convenient one-step procedure, high stereoselectivity, and good functional-group tolerance.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 13","pages":"Pages 3347-3352"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3856265","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stereoselective synthesis of five- and six-membered carbocycles via Matteson homologation/ring closing metathesis† 通过Matteson同系物/闭环复分解立体选择性合成五元和六元碳环†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00457k
Thorsten Kinsinger , Uli Kazmaier
{"title":"Stereoselective synthesis of five- and six-membered carbocycles via Matteson homologation/ring closing metathesis†","authors":"Thorsten Kinsinger ,&nbsp;Uli Kazmaier","doi":"10.1039/d3qo00457k","DOIUrl":"10.1039/d3qo00457k","url":null,"abstract":"<div><p>The Matteson homologation is found to be a versatile tool for the stereoselective synthesis of polyunsaturated alkyl boronic esters, which are excellent precursors for the construction of five- and six-membered carbocycles <em>via</em> ring-closing metathesis. The high diversity of the Matteson reaction allows for the preparation of highly substituted cyclic boronic esters, which are also suitable for further homologations.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 2963-2967"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2023/qo/d3qo00457k?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694187","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Zinc-catalyzed desymmetric hydrosilylation of monosubstituted malonic esters† 锌催化的单取代丙二酸酯的去对称氢化硅烷化†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo02055f
Yixiao Zhang , Pengwei Xu , Qiongli Zhao , Jun (Joelle) Wang , Zhongxing Huang
{"title":"Zinc-catalyzed desymmetric hydrosilylation of monosubstituted malonic esters†","authors":"Yixiao Zhang ,&nbsp;Pengwei Xu ,&nbsp;Qiongli Zhao ,&nbsp;Jun (Joelle) Wang ,&nbsp;Zhongxing Huang","doi":"10.1039/d2qo02055f","DOIUrl":"10.1039/d2qo02055f","url":null,"abstract":"<div><p>Substituted malonic esters are valuable substrates for desymmetrization to tertiary and quaternary stereocenters, as they can be easily accessed <em>via</em> substitution and the resulting chiral monoesters are versatile building blocks and prevalent motifs in bioactive molecules. Here, building upon a previously reported dinuclear zinc-catalyzed asymmetric hydrosilylation that generated quaternary stereocenters, a pipecolinol-derived tetradentate ligand was devised to extend the desymmetric protocol to monosubstituted malonic esters. This new variation of the desymmetrization has allowed the preparation of structurally diverse tertiary stereocenters in good yields and enantioselectivity. The synthetic utility of these enantioenriched products has also been illustrated in a mild amination procedure to synthesize chiral amino alcohols.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1675-1679"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694166","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols† 钌催化的1,3-吲哚基在α，α-二取代烯丙醇中的迁移
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00049d
Xue Zhang , Zhen Luo , Tang-Lin Liu , Qing-Hua Li
{"title":"Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols†","authors":"Xue Zhang ,&nbsp;Zhen Luo ,&nbsp;Tang-Lin Liu ,&nbsp;Qing-Hua Li","doi":"10.1039/d3qo00049d","DOIUrl":"10.1039/d3qo00049d","url":null,"abstract":"<div><p>The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less reported. Herein, we report a protocol for Ru-catalyzed 1,3-indolyl migration under mild conditions. In this study, we disclosed that indoles have better migration ability than phenyl groups. Overall, this catalytic system enabled the simultaneous selective C(sp<sup>3</sup>)–C(sp<sup>2</sup>) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 7","pages":"Pages 1705-1709"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3694171","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Exploration of N-hydroxy benzimidazole catalysts for hydrogen atom transfer reactions† 用于氢原子转移反应的N-羟基苯并咪唑催化剂的探索†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01860h
Zhi-Xian Wu , Xue-Tao Xu , Yu-Xin Luan
{"title":"Exploration of N-hydroxy benzimidazole catalysts for hydrogen atom transfer reactions†","authors":"Zhi-Xian Wu ,&nbsp;Xue-Tao Xu ,&nbsp;Yu-Xin Luan","doi":"10.1039/d2qo01860h","DOIUrl":"10.1039/d2qo01860h","url":null,"abstract":"<div><p><em>N</em>-Hydroxy benzimidazoles (NHBIs) have proved to be efficient hydrogen atom abstractors (HAAs), but their further application in catalysis has been rarely explored since the first report. Herein, we describe their catalytic performance in other hydrogen atom transfer reactions. Specifically, we realized a copper/NHBI co-catalyzed synthesis of 2-phosphonopyrroles <em>via</em> cascade [3 + 2] annulation–aromatization. And NHBI was demonstrated to play a crucial role in both the annulation step and the subsequent aromatization. Besides, NHBI-catalyzed annulation with an imine and C–H oxidation were also feasible. Notably, NHBIs bearing a docking group that can recognize substrates were also investigated as bifunctional HAT catalysts for the first time.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 6","pages":"Pages 1429-1434"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3865593","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enantioselective Ni-catalyzed syn-hydrometalative cyclization of alkyne-tethered ketoamides to α-hydroxy-γ-lactams†‡ 对映体选择性Ni催化炔烃连接的酮酰胺的同氢盐环化反应生成α-羟基-γ-内酰胺††
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00670k
Hai-Xiang Zeng , Xiao-Wen Zhang , Qi-Yang Li , Wen-Bo Liu
{"title":"Enantioselective Ni-catalyzed syn-hydrometalative cyclization of alkyne-tethered ketoamides to α-hydroxy-γ-lactams†‡","authors":"Hai-Xiang Zeng ,&nbsp;Xiao-Wen Zhang ,&nbsp;Qi-Yang Li ,&nbsp;Wen-Bo Liu","doi":"10.1039/d3qo00670k","DOIUrl":"10.1039/d3qo00670k","url":null,"abstract":"<div><p>An enantioselective Ni-catalyzed <em>syn</em>-hydrocyclization of alkyne-tethered ketoamides for the synthesis of α-hydroxy γ-lactams is reported. Using Ni(OTs)<sub>2</sub>·6H<sub>2</sub>O/(<em>S</em>,<em>S</em>)-Me-Duphos as a precatalyst and (EtO)<sub>2</sub>MeSiH as a hydride source, a broad range of enantioenriched γ-lactams with a fully substituted stereogenic center are obtained in 32–84% yields with 87.5 : 12.5–97 : 3 er. Synthetic utilities, including scale-up reaction and product derivatization, are also demonstrated. This research presents a regioselective functionalization of alkynes and provides an efficient strategy to access functional group-enriched chiral heterocycles.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3883-3888"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3865634","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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