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Formal [5 + 2] cycloaddition of ortho-indolizinyl anilines with cyclopentenediones: access to planar indolizine-fused azepines† 邻位中氮茚基苯胺与环戊烯二酮的形式[5+2]环加成：获得平面中氮茚-稠合氮杂环丙烷†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00266g
Qijian Ni , Lirong Zhang , Zhiming Zhu , Xiaoxiao Song
{"title":"Formal [5 + 2] cycloaddition of ortho-indolizinyl anilines with cyclopentenediones: access to planar indolizine-fused azepines†","authors":"Qijian Ni ,&nbsp;Lirong Zhang ,&nbsp;Zhiming Zhu ,&nbsp;Xiaoxiao Song","doi":"10.1039/d3qo00266g","DOIUrl":"10.1039/d3qo00266g","url":null,"abstract":"<div><p>An efficient and straightforward approach to planar indolizine-fused azepines <em>via</em> Brønsted acid catalyzed [5 + 2] cycloaddition of <em>ortho</em>-indolizinyl anilines with cyclopentenediones has been established. This reaction involves a Friedel–Crafts addition/oxidation/Schiff-base condensation tandem process and features mild conditions, broad substrate scope and diverse further transformations. Furthermore, the intriguing planar azepines exhibited favorable photoluminescence properties, which indicated their potential as fluorescent materials.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 10","pages":"Pages 2526-2531"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830485","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
Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide† 2-芳氧基和2-芳基羧酸与N-硒代氰邻苯二甲酰亚胺的光催化脱羧硒代氰†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00347g
Yong Gao , Ruirui Hua , Hongquan Yin , Fu-Xue Chen
{"title":"Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide†","authors":"Yong Gao ,&nbsp;Ruirui Hua ,&nbsp;Hongquan Yin ,&nbsp;Fu-Xue Chen","doi":"10.1039/d3qo00347g","DOIUrl":"10.1039/d3qo00347g","url":null,"abstract":"<div><p>A visible-light-induced decarboxylative selenocyanation reaction of aliphatic carboxylic acids for the formation of C(sp<sup>3</sup>)–SeCN bonds has been developed. The electrophilic <em>N</em>-selenocyanatophthalimide and a pyrylium salt were applied as a SeCN radical precursor and an organic photocatalyst, respectively. The transformation could proceed smoothly without transition metals, oxidants and additional bases, affording the corresponding alkyl selenocyanates in moderate to good yields. This method is characterized by its simplicity, wide substrate scope and mild conditions.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 10","pages":"Pages 2538-2543"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830487","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
Sequence-selective three-component reactions of alkyltrifluoroborates with α,β-unsaturated carbonyl compounds and vinylphosphonium salts† 烷基三氟硼酸盐与α，β-不饱和羰基化合物和乙烯基鏻盐的序列选择性三组分反应†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00631j
Masaki Yoshida , Masaya Sawamura , Yusuke Masuda
{"title":"Sequence-selective three-component reactions of alkyltrifluoroborates with α,β-unsaturated carbonyl compounds and vinylphosphonium salts†","authors":"Masaki Yoshida ,&nbsp;Masaya Sawamura ,&nbsp;Yusuke Masuda","doi":"10.1039/d3qo00631j","DOIUrl":"10.1039/d3qo00631j","url":null,"abstract":"<div><p>A photocatalytic three-component reaction of alkyltrifluoroborates with two different electron-deficient alkenes has been developed. The addition reaction occurs sequentially with α,β-unsaturated carbonyl compounds and vinyltriphenylphosphonium bromide in this order to produce α-branched γ-phosphoniocarbonyl compounds. The reaction could be followed by stereoselective Wittig olefination with various aldehydes to afford structurally diverse α-branched γ,δ-unsaturated ketones and esters with a <em>Z</em>-configuration. Mechanistic investigations suggested that boron trifluoride generated from the organotrifluoroborate activates the α,β-unsaturated carbonyl compound to facilitate the first chemoselective radical addition. We assume that the high efficiency of the second addition with the vinylphosphonium salt might arise from electrostatic interactions caused by the positive charge of the phosphonio group.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 14","pages":"Pages 3654-3661"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830494","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
Ni-catalyzed regioselective hydrobenzylation of alkenes to afford C(sp3)–C(sp3) bonds using BH3 as a reductant† 使用BH3作为还原剂，Ni催化烯烃的区域选择性加氢苄基化以提供C（sp3）–C（sp三）键†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01510b
Li Cheng , Quan Lin , Yanhong Song , Hua Chen , Hegui Gong , Yunrong Chen
{"title":"Ni-catalyzed regioselective hydrobenzylation of alkenes to afford C(sp3)–C(sp3) bonds using BH3 as a reductant†","authors":"Li Cheng ,&nbsp;Quan Lin ,&nbsp;Yanhong Song ,&nbsp;Hua Chen ,&nbsp;Hegui Gong ,&nbsp;Yunrong Chen","doi":"10.1039/d2qo01510b","DOIUrl":"10.1039/d2qo01510b","url":null,"abstract":"<div><p>The nickel-catalyzed reductive olefin hydrocarbonation reaction is one of the powerful tools for the formation of C(sp<sup>3</sup>)–C bonds. However, the reductive coupling of alkenes with benzyl halides to afford alkyl–benzyl products has rarely been studied using the well-established Ni/SiH methods. Herein, we report a method of Ni-catalyzed regioselective hydrobenzylation of unactivated alkenes to afford anti-Markovnikov products using BH<sub>3</sub> as a reductant. This method exhibits good functional group tolerance, a wide scope and high regioselectivity. The mild conditions enable the coupling of terminal and internal alkenes with primary and secondary benzyl halides.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 2","pages":"Pages 369-374"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830499","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: 1
Visible-light-promoted generation of p-(N,N-dimethyl)benzyl equivalents and their reactions with quinols: easy access to diarylalkanes† 可见光促进对-（N，N-二甲基）苄基当量的产生及其与喹啉的反应：容易获得二芳基烷烃†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01906j
Baihui Zheng , Xiaotong Li , Shuyang Meng , Yifei Li , Qun Liu , Ling Pan
{"title":"Visible-light-promoted generation of p-(N,N-dimethyl)benzyl equivalents and their reactions with quinols: easy access to diarylalkanes†","authors":"Baihui Zheng ,&nbsp;Xiaotong Li ,&nbsp;Shuyang Meng ,&nbsp;Yifei Li ,&nbsp;Qun Liu ,&nbsp;Ling Pan","doi":"10.1039/d2qo01906j","DOIUrl":"10.1039/d2qo01906j","url":null,"abstract":"<div><p>The development and applications of novel synthetic intermediates are essential for synthetic chemistry. α-Amino alkyl radicals have been proven to be promising synthetic intermediates for the construction of versatile natural products and drugs. However, high reduction potentials of imines and further oxidation of the generated α-amino alkyl radicals limit their applications. Herein, we reveal the highly selective generation of <em>p</em>-(<em>N</em>,<em>N</em>-dimethyl)benzyl equivalents from easily-available <em>N</em>,<em>N</em>-dimethyl arylamines <em>via</em> α-amino alkyl radicals in the presence of the iridium photosensitizer without any other additives. A series of trifluoromethyl-containing diarylalkanes were obtained in good to high yields from the visible-light-promoted reaction of <em>N</em>,<em>N</em>-dimethyl arylamines and quinols under very mild reaction conditions. The route provides novel access to trifluoromethyl-containing arenes under environment-friendly conditions.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 4","pages":"Pages 859-865"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830527","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
Rhodium-catalyzed aminoacylation of alkenes via carbonylative C–H activation toward poly(hetero)cyclic alkylarylketones† 铑催化烯烃通过羰基化C–H活化对聚（杂）环烷基芳烯酮的氨基酰化†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01777f
Chao Yang , Lijun Shi , Wenlong Wang , Ji-Bao Xia , Fuwei Li
{"title":"Rhodium-catalyzed aminoacylation of alkenes via carbonylative C–H activation toward poly(hetero)cyclic alkylarylketones†","authors":"Chao Yang ,&nbsp;Lijun Shi ,&nbsp;Wenlong Wang ,&nbsp;Ji-Bao Xia ,&nbsp;Fuwei Li","doi":"10.1039/d2qo01777f","DOIUrl":"10.1039/d2qo01777f","url":null,"abstract":"<div><p>The well-developed carbonylative synthesis of varied and useful complex molecules with CO is very efficient and attractive. Herein, rhodium-catalyzed modular carbonylative aminobenzoylation of alkenes with a pendant acylaniline enabled by dual cleavage of N–H bonds and C–H bonds under ambient pressure of CO/O<sub>2</sub> was developed. Various poly(hetero)cyclic alkylarylketones were obtained in moderate-to-high yields. The logical synthetic transformations of products were also explored.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 4","pages":"Pages 872-879"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3830529","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
Domino Sonogashira coupling/metal carbene-involved annulation enabled by Pd/Cu relay catalysis: rapid assembly of indazole-containing biheteroaryls† Domino Sonogashira偶联/金属卡宾参与Pd/Cu中继催化的环化：含吲唑双杂芳基的快速组装†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00367a
Ruiming Ding , Haili Cui , Yongyan Zhu , Yao Zhou , Huaming Tao , Shaoyu Mai
{"title":"Domino Sonogashira coupling/metal carbene-involved annulation enabled by Pd/Cu relay catalysis: rapid assembly of indazole-containing biheteroaryls†","authors":"Ruiming Ding ,&nbsp;Haili Cui ,&nbsp;Yongyan Zhu ,&nbsp;Yao Zhou ,&nbsp;Huaming Tao ,&nbsp;Shaoyu Mai","doi":"10.1039/d3qo00367a","DOIUrl":"10.1039/d3qo00367a","url":null,"abstract":"<div><p>An efficient and novel method has been developed for the synthesis of indazole-containing biheteroaryls <em>via</em> a domino Sonogashira coupling/azaenyne cycloisomerization/Barton–Kellogg reaction. The new scalable protocol leads to a broad array of substituted indazole-containing biheteroaryls under mild reaction conditions. Compared to classical domino Sonogashira coupling/cyclization, this powerful strategy enables simultaneous generation of two heterocycles, especially the two C-atoms of a terminal alkyne are, respectively, incorporated into two different rings. Preliminary mechanistic studies demonstrate that the CuI catalyst has multiple roles, guaranteeing the connection of each reaction smoothly. Remarkably, this work represents an unprecedented example of domino Sonogashira coupling/metal carbene-involved annulation.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2171-2176"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3840399","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
Ligand-controlled regiodivergence in cobalt-catalyzed hydrosilylation of isoprene† 钴催化异戊二烯硅氢化反应中配体控制的区域聚集†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00041a
Sa-Na Yang , Chang-Hui Liu , Li-Bowen He , Hao Zheng , Chang-Sheng Kuai , Boshun Wan , Ding-Wei Ji , Qing-An Chen
{"title":"Ligand-controlled regiodivergence in cobalt-catalyzed hydrosilylation of isoprene†","authors":"Sa-Na Yang ,&nbsp;Chang-Hui Liu ,&nbsp;Li-Bowen He ,&nbsp;Hao Zheng ,&nbsp;Chang-Sheng Kuai ,&nbsp;Boshun Wan ,&nbsp;Ding-Wei Ji ,&nbsp;Qing-An Chen","doi":"10.1039/d3qo00041a","DOIUrl":"10.1039/d3qo00041a","url":null,"abstract":"<div><p>In this article, we disclose a method for the regiodivergent and stereoselective hydrosilylation of isoprene using an Earth-abundant cobalt catalyst <em>via</em> variation of ligands. With a less sterically hindered bidentate ligand, the reactions proceeded through 4,1-hydrosilylation to afford allylsilanes in excellent regio- and stereoselectivities. By switching to a bulkier ligand, the reactions were efficiently diverted to 2,1-addition products for the first time. This regiodivergent protocol provides a modular approach for the construction of structurally diverse organosilanes with high atom economy and without the formation of stoichiometric byproducts.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 9","pages":"Pages 2204-2210"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3840404","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
The role of attractive dispersion interaction in promoting the catalytic activity of asymmetric hydrogenation† 吸引分散相互作用在促进不对称氢化催化活性中的作用†
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d3qo00332a
Limin Yang , Bo Li , K.N. Houk
{"title":"The role of attractive dispersion interaction in promoting the catalytic activity of asymmetric hydrogenation†","authors":"Limin Yang ,&nbsp;Bo Li ,&nbsp;K.N. Houk","doi":"10.1039/d3qo00332a","DOIUrl":"10.1039/d3qo00332a","url":null,"abstract":"<div><p>As an essential van der Waals interaction, the dispersion interaction is an important weak attractive interaction. However, the influence of the weak attractive interactions has only recently been elucidated in transition metal catalyzed asymmetric hydrogenations by the Wanbin Zhang group. Our IGM/EDA analysis proves Zhang's finding that attractive interactions play an important role in asymmetric hydrogenation, which provides new strategies for the sophisticated design of chiral transition metal catalysts. The dispersion interaction is the major weak attractive interaction that activates the asymmetric hydrogenations by favorable interactions of substrate and metal catalyst.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 14","pages":"Pages 3485-3490"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3840420","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
Exploring visible light for carbon–nitrogen and carbon–oxygen bond formation via nickel catalysis 探索可见光通过镍催化形成碳-氮和碳-氧键
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI: 10.1039/d2qo01700h
Shengqing Zhu , Huan Li , Yingying Li , Zhonghou Huang , Lingling Chu
{"title":"Exploring visible light for carbon–nitrogen and carbon–oxygen bond formation via nickel catalysis","authors":"Shengqing Zhu ,&nbsp;Huan Li ,&nbsp;Yingying Li ,&nbsp;Zhonghou Huang ,&nbsp;Lingling Chu","doi":"10.1039/d2qo01700h","DOIUrl":"10.1039/d2qo01700h","url":null,"abstract":"<div><p>Heteroatom-containing motifs are one of the most privileged scaffolds for pharmaceuticals, agrochemicals, and functional materials. Transition-metal-catalyzed carbon–heteroatom bond-forming reactions have emerged as an indispensable synthetic tool for the rapid assembly of these valuable skeletons. Despite impressive progress, the development of general and efficient methods for the catalytic construction of carbon–heteroatom bonds with Earth-abundant catalysts under mild conditions is still highly desirable. Utilizing the new and unique reactivity uncovered by photoexcitation, recently, exciting progress has been made in the area of visible-light-driven nickel-catalyzed carbon–heteroatom bond-forming reactions, enabling facile access to diverse carbon–heteroatom bonds under exceptionally mild conditions. In this review, we highlight the recent synthetic methodology development for the formation of C–N and C–O bonds <em>via</em> visible-light-driven high-valent nickel complexes or photoexcited nickel complexes, with in-depth discussions with reaction designs and mechanistic scenarios.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 2","pages":"Pages 548-569"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"3840436","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: 1
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