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Catalyst-Free Regio- and Stereoselective C(sp2)–H Chlorination of Enamides at Room Temperature 室温下无催化剂区域和立体选择性C(sp2) - h氯化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-29 DOI: 10.1021/acs.orglett.5c01110
Meng-Liang Deng, Meng-Wei Sheng, Xu-Kang Wen, Ruo-Nan Cao, Meng Li, Teck-Peng Loh, Ming-Zhu Lu
{"title":"Catalyst-Free Regio- and Stereoselective C(sp2)–H Chlorination of Enamides at Room Temperature","authors":"Meng-Liang Deng, Meng-Wei Sheng, Xu-Kang Wen, Ruo-Nan Cao, Meng Li, Teck-Peng Loh, Ming-Zhu Lu","doi":"10.1021/acs.orglett.5c01110","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01110","url":null,"abstract":"We disclose herein a catalyst-free, room-temperature protocol for the highly regio- and stereoselective alkenyl C(sp<sup>2</sup>)–H chlorination of diverse enamides with commercially available, inexpensive <i>N</i>-chlorosuccinimide (NCS) as the electrophilic chlorinating reagent under exceedingly mild conditions. This operationally simple approach features a remarkably broad substrate scope and accommodates excellent functional group tolerance, affording a diverse range of synthetically valuable geometrically defined β-chlorinated enamides in high yields with an exclusive <i>E</i> configuration.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"104 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enantioselective Synthesis of N-Substituted Indoles with α,β-Stereocenters via Sequential Aza-Piancatelli/Cyclization Reactions 序贯Aza-Piancatelli/环化反应对映选择性合成具有α，β-立体中心的n -取代吲哚
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-29 DOI: 10.1021/acs.orglett.5c01381
Kaijun Xie, Xukun Nie, Pengfei Zhou, Yurong Tang, Yunfei Cai
{"title":"Enantioselective Synthesis of N-Substituted Indoles with α,β-Stereocenters via Sequential Aza-Piancatelli/Cyclization Reactions","authors":"Kaijun Xie, Xukun Nie, Pengfei Zhou, Yurong Tang, Yunfei Cai","doi":"10.1021/acs.orglett.5c01381","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01381","url":null,"abstract":"A sequence of catalytic asymmetric aza-Piancatelli rearrangement and Pd-catalyzed cyclization has been developed to construct chiral <i>N</i>-substituted indoles featuring α,β-consecutive stereocenters. This indole framework, bearing α,β-chiral centers, is a prevalent structural motif in natural products and biologically active molecules, yet catalytic enantioselective methods for its preparation remain scarce. This protocol offers efficient access to a diverse array of <i>N</i>-substituted indole derivatives with α,β-consecutive stereocenters, achieving high yields and excellent enantioselectivities.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890202","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ni(II)-Catalyzed Site- and Regioselective α-Alkenylation of Cyclic Ketones with Alkenes Ni(II)-催化环酮与烯烃的位点选择性和区域选择性α-烯化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-29 DOI: 10.1021/acs.orglett.5c00745
Tongtong Ni, Xuefeng Xu, Man Cao, Mengfan Chang, Wenguang Li, Xu Zhang, Fengyun Su, Ting Li
{"title":"Ni(II)-Catalyzed Site- and Regioselective α-Alkenylation of Cyclic Ketones with Alkenes","authors":"Tongtong Ni, Xuefeng Xu, Man Cao, Mengfan Chang, Wenguang Li, Xu Zhang, Fengyun Su, Ting Li","doi":"10.1021/acs.orglett.5c00745","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00745","url":null,"abstract":"Herein, a nickel-catalyzed α-alkenylation reaction of asymmetric cyclic ketones at the sterically hindered α-position with alkenes is disclosed. The high regioselectivity might originate from the acid-catalyzed enolization reaction, selectively generating the thermodynamically favored enol. The nickel catalyst facilitates the preferential alkenylation of polysubstituted enolates rather than monosubstituted enolates, thereby reversing the conventional regioselectivity of alkenylation at the α-position of ketones. This method encompasses a broad range of applicable substrates of alkenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"39 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143890200","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Base Mediated 1,2-Carboboration: Direct Access to Multisubstituted Alkenyl and Alkylboronates 碱介导的1,2-碳硼化：直接获得多取代的烯基和烷基硼酸盐
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-29 DOI: 10.1021/acs.orglett.5c01382
Suma Basappa, Aishwarya Prakash, Adithya K. P., Manoj V. Mane, Shubhankar Kumar Bose
{"title":"Base Mediated 1,2-Carboboration: Direct Access to Multisubstituted Alkenyl and Alkylboronates","authors":"Suma Basappa, Aishwarya Prakash, Adithya K. P., Manoj V. Mane, Shubhankar Kumar Bose","doi":"10.1021/acs.orglett.5c01382","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01382","url":null,"abstract":"We have developed a base-mediated 1,2-carboboration of commercially accessible alkynes for the construction of regio- and stereodefined alkenylboronates. This unprecedented reaction is enabled by sodium ethoxide (NaOEt) as a base and alkyl halide as an electrophile, with B<sub>2</sub>pin<sub>2</sub> under mild reaction conditions. The protocol is simple, clean, and more economical compared to reported transition metal-catalyzed systems. The highlights of this methodology include readily available precursors, broad substrate scope and functional group compatibility, gram scale synthesis, and late-stage functionalization of alkenylboronates. The reaction is also applicable for the carboboration of alkenes. Experimental results and density functional theory (DFT) calculations provide insights into the mechanism.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143885177","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
1-Arylallyloxysilanes as Formal Precursors to Ketone-Derived Potassium Homoenolate Equivalents 1-芳烯丙烯氧基硅烷作为酮衍生的同烯酸钾等价物的形式前体
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-28 DOI: 10.1021/acs.orglett.5c01177
Shuto Okuda, Yutaka Narita, Rikuo Hayashi, Taro Udagawa, Masahiro Sai
{"title":"1-Arylallyloxysilanes as Formal Precursors to Ketone-Derived Potassium Homoenolate Equivalents","authors":"Shuto Okuda, Yutaka Narita, Rikuo Hayashi, Taro Udagawa, Masahiro Sai","doi":"10.1021/acs.orglett.5c01177","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01177","url":null,"abstract":"This paper reports the successful conversion of 1-arylallyloxysilanes into highly nucleophilic siloxyallylpotassium intermediates using (trimethylsilyl)methylpotassium as the base. These organopotassium species react regioselectively with various electrophiles, leading to the formation of the corresponding 3-functionalized (<i>Z</i>)-silyl enol ethers. The resulting silyl enol ethers can undergo a range of α-functionalization reactions, yielding ketones with diverse structures. Thus, our method enables the effective utilization of 1-arylallyloxysilanes as formal precursors to ketone-derived potassium homoenolate equivalents.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143880871","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Asymmetric Organocatalytic [3 + 2]-Cycloaddition of N-Alkoxy-4-oxo-acrylamides with Isatin-Derived Ketimines: Access to Enantioselective Synthesis of Spirooxindole-imidazolidinones 不对称有机催化[3 + 2]- n-烷氧基-4-氧丙烯酰胺与isatin衍生的酮胺的环加成反应：对映选择性合成spirooxindoli -咪唑烷酮的途径
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-27 DOI: 10.1021/acs.orglett.5c01076
Ji Won Han, Yeongju Kim, Donggeon Kim, Dongwook Kim, Sung-Gon Kim
{"title":"Asymmetric Organocatalytic [3 + 2]-Cycloaddition of N-Alkoxy-4-oxo-acrylamides with Isatin-Derived Ketimines: Access to Enantioselective Synthesis of Spirooxindole-imidazolidinones","authors":"Ji Won Han, Yeongju Kim, Donggeon Kim, Dongwook Kim, Sung-Gon Kim","doi":"10.1021/acs.orglett.5c01076","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01076","url":null,"abstract":"The spirooxindole framework is a privileged motif in numerous biologically significant natural products and has been demonstrated as a crucial core scaffold in a variety of medicinally significant compounds. Herein, we achieved a highly efficient enantioselective [3 + 2]-cycloaddition reaction of <i>N</i>-alkoxy-4-oxo-acrylamides with isatin-derived ketimines. This method enabled the precise synthesis of chiral spirooxindole-imidazolidinone derivatives, which are notable for their intricate structures and the presence of chiral quaternary centers. Our approach utilized an organocatalytic strategy with a hydrogen-bonding bifunctional squaramide-based catalyst. This reaction demonstrated impressive results, achieving high yields and exceptional enantioselectivities of &gt;99% ee for the majority of substrates, even when employing only 2 mol % of the catalyst.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"70 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143880873","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Dialkylation of 1,3-Dienes with Aldehydes and Cyclopropanols toward Homoallylic Alcohols by Dual Photoredox and Chromium Catalysis 双光氧化还原和铬催化1,3-二烯与醛和环丙醇二烷基化制同丙烯醇
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-27 DOI: 10.1021/acs.orglett.5c00975
Gaochen Xu, Pei Guan, Longyu Deng, Caipeng Wang, Delong Ma, Yan Meng, Zheng Fang, Jindian Duan, Kai Guo
{"title":"Dialkylation of 1,3-Dienes with Aldehydes and Cyclopropanols toward Homoallylic Alcohols by Dual Photoredox and Chromium Catalysis","authors":"Gaochen Xu, Pei Guan, Longyu Deng, Caipeng Wang, Delong Ma, Yan Meng, Zheng Fang, Jindian Duan, Kai Guo","doi":"10.1021/acs.orglett.5c00975","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00975","url":null,"abstract":"A visible-light-induced three-component coupling of aldehydes, 1,3-dienes, and cyclopropyl alcohols using dual photoredox and chromium catalysis is herein described. This efficient protocol achieves the dialkylation of 1,3-dienes toward 1,4-disubstituted homoallylic alcohols in moderate to good yields with excellent regioselectivity, featuring mild reaction conditions, good functional group tolerance, and gram-scale synthesis. Mechanistic study suggests that photoinduced sequential ring opening of cyclopropyl alcohol and radical and nucleophilic cascade addition are involved in the catalytic cycle.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143880872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Catalytic Generation of o-Quinone Dimethides by a Nondiazo Approach via Donor/Donor Platinum Carbenes 非重氮法通过给体/给体铂卡贝烯催化生成邻醌二甲醚
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-27 DOI: 10.1021/acs.orglett.5c01508
Jun-Jie Hao, Tao Jiang, FuJunyang Wu, Hejiang Luo, Rong-Tao Li
{"title":"Catalytic Generation of o-Quinone Dimethides by a Nondiazo Approach via Donor/Donor Platinum Carbenes","authors":"Jun-Jie Hao, Tao Jiang, FuJunyang Wu, Hejiang Luo, Rong-Tao Li","doi":"10.1021/acs.orglett.5c01508","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01508","url":null,"abstract":"A platinum-catalyzed reaction of enynones with various dienophiles has been developed for the construction of tetrahydronaphthalene derivatives, which undergo a Diels–Alder reaction process with platinum carbenes and <i>o</i>-quinone dimethide (<i>o-</i>QDM) intermediates. In this protocol, an alkoxy-substituted conjugated enynone is used as a nondiazo carbene precursor for the generation of <i>o-</i>QDMs, thereby extending the methods available for the generation of <i>o-</i>QDMs. The reaction is characterized by its high atom economy, high diastereoselectivity, and broad substrate scope.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"6 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143878035","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Gold/Copper Dual-Catalyzed Annulation of Arynes with Phosphites: A Synthetic Strategy for Dibenzophospholes 金/铜双催化苯乙烯与亚磷酸盐环化：二苯并膦孔的合成策略
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-27 DOI: 10.1021/acs.orglett.5c01178
Donghwa Shin, Seo-Jung Han
{"title":"Gold/Copper Dual-Catalyzed Annulation of Arynes with Phosphites: A Synthetic Strategy for Dibenzophospholes","authors":"Donghwa Shin, Seo-Jung Han","doi":"10.1021/acs.orglett.5c01178","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01178","url":null,"abstract":"A synthetic approach to dibenzophospholes was developed via the gold- and copper-catalyzed annulation reactions of arynes and phosphites. The reaction conditions demonstrated a broad functional group tolerance, enabling the synthesis of a diverse range of dibenzophosphole 5-oxides. This method is useful for preparing dibenzophospholes with unique optical and electronic properties.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"7 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143878031","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Heterogeneous g-C3N4/NaI Dual Catalytic Difunctionalization of Alkenes with Heteroarenes and Methyl Carbazate under Visible Light 可见光下g-C3N4/NaI双催化烯烃与杂芳烃和氨基甲酸甲酯的双官能化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-26 DOI: 10.1021/acs.orglett.5c01200
Kai Zheng, Chao Chen, Yacong Wang, Hao Xu, Kai Ge, Chao Shen
{"title":"Heterogeneous g-C3N4/NaI Dual Catalytic Difunctionalization of Alkenes with Heteroarenes and Methyl Carbazate under Visible Light","authors":"Kai Zheng, Chao Chen, Yacong Wang, Hao Xu, Kai Ge, Chao Shen","doi":"10.1021/acs.orglett.5c01200","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01200","url":null,"abstract":"Herein, a photoinduced heterogeneous catalytic system merging g-C<sub>3</sub>N<sub>4</sub> and NaI has been established for the difunctionalization of alkenes in conjunction with heteroarenes and methyl carbazate. This approach is notable for its broad substrate tolerance, encompassing a wide range of alkenes and heteroarenes and leading to the formation of the corresponding esters with moderate to good yields. Additionally, the scalability of the synthetic process and the versatility of the product transformations have been illustrated, highlighting its potential for practical application in organic synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"53 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143876274","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","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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