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CuOTf(Tol)1/2-Catalyzed O-Trifluoroethylation of Alcohols with 2,2,2-Trifluorodiazoethane
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-21 DOI: 10.1021/acs.orglett.5c00942
Leyi Tao, Zhiyu Lei, Lianyun Zhao, Tao Ji, Yeon-Hee Lim, James Patrick Roane, Bin Hu, Xin Wen
{"title":"CuOTf(Tol)1/2-Catalyzed O-Trifluoroethylation of Alcohols with 2,2,2-Trifluorodiazoethane","authors":"Leyi Tao, Zhiyu Lei, Lianyun Zhao, Tao Ji, Yeon-Hee Lim, James Patrick Roane, Bin Hu, Xin Wen","doi":"10.1021/acs.orglett.5c00942","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00942","url":null,"abstract":"Trifluoroethyl groups are important in medicinal chemistry since they can impart desirable properties, such as enhanced lipophilicity, metabolic stability, or binding affinity. A practical and scalable protocol has been developed for O-trifluoroethylation of alcohols with 2,2,2-trifluorodiazoethane using Cu(OTf)(Tol)<sub>1/2</sub> catalyst under mild conditions. This novel approach demonstrated high reactivity and broad substrate scope toward a diverse range of alcohols, ranging from fused and bridged ring systems, linear alcohols, to even sugar motifs, which makes the protocol valuable for medicinal chemistry, material science, and other areas where the introduction of trifluoroethyl groups would be beneficial.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853597","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
Tetrafluoropyridine Regulated Site-Selective Cycloaddition of Diazoacetates with 1,4-Unsymmetrical [60]Fullerene Adducts
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-21 DOI: 10.1021/acs.orglett.5c00914
Sheng-Hu Yuan, Meng-Ran Li, Zheng-Chun Yin, Jun Xuan, Hongping Zhou, Fei Li
{"title":"Tetrafluoropyridine Regulated Site-Selective Cycloaddition of Diazoacetates with 1,4-Unsymmetrical [60]Fullerene Adducts","authors":"Sheng-Hu Yuan, Meng-Ran Li, Zheng-Chun Yin, Jun Xuan, Hongping Zhou, Fei Li","doi":"10.1021/acs.orglett.5c00914","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00914","url":null,"abstract":"Site-selective multiple addition reactions of fullerenes hold great promise for generating new nanocarbons with diverse material and biological applications. However, there are a lack of strategies for achieving site selectivity in a stepwise manner within this field. In this study, we discovered that tetrafluoropyridine-modified unsymmetrical 1,4-C<sub>60</sub> adducts can undergo highly site-selective cycloadditions with diazoacetates. This finding suggests that leveraging the 1,4-unsymmetric bifunctional group effect can be an effective strategy for controlling the regioselectivity for further reactions of 1,4-(organo)[60]fullerene.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"63 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853596","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
Dual Photoexcited Palladium and Photoredox-Catalyzed Remote C(sp3)–H Acylation of Hydroxyamides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-20 DOI: 10.1021/acs.orglett.5c00881
Daling Li, Jun Wei, Lixu Ren, Lingmin Zhou, Liya Huang, Ying Yu, Siping Wei, Na Hao, Jun Wang, Lin Yang, Xianchao Pan, Qiang Fu, Ji Lu
{"title":"Dual Photoexcited Palladium and Photoredox-Catalyzed Remote C(sp3)–H Acylation of Hydroxyamides","authors":"Daling Li, Jun Wei, Lixu Ren, Lingmin Zhou, Liya Huang, Ying Yu, Siping Wei, Na Hao, Jun Wang, Lin Yang, Xianchao Pan, Qiang Fu, Ji Lu","doi":"10.1021/acs.orglett.5c00881","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00881","url":null,"abstract":"Herein, we report an unprecedented dual photoexcited palladium and photoredox-catalyzed remote C(sp<sup>3</sup>)–H acylation of amides free of external acylating reagents through sequential N–O/C–H/C–O bond cleavage and chemoselective C–C bond formation. This dual catalytic system shows high efficiency, good atom economy by deletion of oxygen, and diverse functional group tolerance. Experimental investigation of the reaction mechanism revealed that <i>O</i>-acyl hydroxamides enabled by photoexcited palladium generated the alkyl radicals via a 1,5-HAT process mediated by amidyl radicals and a palladium carboxylate complex, which, undergoing photoredox-catalyzed phosphoranyl radical-mediated C–O bond cleavage, leads to coupling with alkyl radicals to deliver the final products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853598","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
Synthesis of the Proposed Structure of Urupocidin A
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-20 DOI: 10.1021/acs.orglett.5c01046
Takuya Tsukamoto, Keisuke Takahashi, Kyoka Someya, Taichi Kusakabe, Keisuke Kato
{"title":"Synthesis of the Proposed Structure of Urupocidin A","authors":"Takuya Tsukamoto, Keisuke Takahashi, Kyoka Someya, Taichi Kusakabe, Keisuke Kato","doi":"10.1021/acs.orglett.5c01046","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01046","url":null,"abstract":"The proposed structure of urupocidin A was synthesized. The bicyclic guanidino core was constructed by Pd(II) catalyzed cyclization-carbonylation-cyclization cascade reactions of the acyclic propargyl guanidine. The <i>N</i>-hydroxy guanidino functionality was protected as a THP ether.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"33 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143853599","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
Aporphinol-Derived Chiral Phosphoric Acids: Synthesis and Catalytic Performance
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-18 DOI: 10.1021/acs.orglett.5c00940
Jun Zhao, Xiuqi Shi, Shuo Tan, Yue Li, Ran Li, Birou Zhang, Hao Song, Fei Xue, Yong Qin
{"title":"Aporphinol-Derived Chiral Phosphoric Acids: Synthesis and Catalytic Performance","authors":"Jun Zhao, Xiuqi Shi, Shuo Tan, Yue Li, Ran Li, Birou Zhang, Hao Song, Fei Xue, Yong Qin","doi":"10.1021/acs.orglett.5c00940","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00940","url":null,"abstract":"A novel series of chiral phosphoric acid (CPA) catalysts based on a bioinspired aporphinol scaffold has been developed. The efficacy of these CPAs is demonstrated through enantioselective transfer hydrogenation of C2-substituted quinolines, achieving excellent enantioselectivities (93–99% enantiomeric excess). They also exhibit catalytic efficiency comparable to that of classic chiral phosphoric acids in the asymmetric Friedel–Crafts reaction and reduction of ketone. This work highlights the potential of aporphinol-based catalysts for diverse asymmetric transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"9 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846677","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
Boronate Formation-Triggered Azide–Alkyne Cycloaddition
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-18 DOI: 10.1021/acs.orglett.5c00732
Jumpei Taguchi, Yohei Ohata, Honoka Akimoto, Hitomi Tabuchi, Kazunobu Igawa, Katsuhiko Tomooka, Takashi Niwa, Takamitsu Hosoya
{"title":"Boronate Formation-Triggered Azide–Alkyne Cycloaddition","authors":"Jumpei Taguchi, Yohei Ohata, Honoka Akimoto, Hitomi Tabuchi, Kazunobu Igawa, Katsuhiko Tomooka, Takashi Niwa, Takamitsu Hosoya","doi":"10.1021/acs.orglett.5c00732","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00732","url":null,"abstract":"A catalyst-free triazole formation reaction between <i>o</i>-borylaryl azides and <i>N</i>-propargyldiethanolamine derivatives is reported. Control experiments demonstrated that the triazole formation was triggered by boronate formation, which brought the azido group and alkyne moiety into close proximity. This boronate formation-triggered azide–alkyne cycloaddition (BAAC) reaction exhibited orthogonality to other azide–alkyne cycloaddition reactions, enabling sequential double-click conjugations with diazido or dialkyne compounds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846492","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
Visible-Light-Accelerated Decarboxylative N-Allylation of γ-Methylidene-δ-valerolactones via Synergistic Pd(0)/Cu(II)/Riboflavin Catalysis
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-18 DOI: 10.1021/acs.orglett.5c01107
Hengchang Yang, Kexin Pang, Bingkun Xue, Xin Li, Ran Song, Daoshan Yang, Wen Si, Jian Lv
{"title":"Visible-Light-Accelerated Decarboxylative N-Allylation of γ-Methylidene-δ-valerolactones via Synergistic Pd(0)/Cu(II)/Riboflavin Catalysis","authors":"Hengchang Yang, Kexin Pang, Bingkun Xue, Xin Li, Ran Song, Daoshan Yang, Wen Si, Jian Lv","doi":"10.1021/acs.orglett.5c01107","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01107","url":null,"abstract":"We report a visible-light-accelerated decarboxylative <i>N</i>-allylation of methylidene-δ-valerolactones via synergistic Pd(0)/Cu(II)/riboflavin catalysis. This method enables efficient coupling of diverse anilines and lactones under mild conditions, achieving an up to 93% yield.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846680","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
Tandem Cu(I)-Catalyzed Dipolar Cycloaddition–C–H Activation for the In-Flow Synthesis of N-Pyridyl-5-amino-1,2,3-triazole-4-carboxylates
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-18 DOI: 10.1021/acs.orglett.5c00453
Emanuela Donato, Martha C. Mayorquín-Torres, Alessandra Puglisi, Maurizio Benaglia, Mauro F. A. Adamo, Christian V. Stevens
{"title":"Tandem Cu(I)-Catalyzed Dipolar Cycloaddition–C–H Activation for the In-Flow Synthesis of N-Pyridyl-5-amino-1,2,3-triazole-4-carboxylates","authors":"Emanuela Donato, Martha C. Mayorquín-Torres, Alessandra Puglisi, Maurizio Benaglia, Mauro F. A. Adamo, Christian V. Stevens","doi":"10.1021/acs.orglett.5c00453","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00453","url":null,"abstract":"A telescoped process under continuous flow conditions is described for the synthesis of <i>N</i>-pyridyl-5-amino-1,2,3-triazole-4-carboxylate derivatives catalyzed by copper salts in a packed bed reactor. The synthetic approach takes first advantage of click chemistry, specifically relying on Cu(I)-catalyzed 1,3-dipolar azide–alkyne cycloaddition (CuAAC), to achieve the efficient and selective assembly of a triazole ring, followed by a copper-mediated C–H activation, that substitutes an inert C–H bond with a C–N bond, providing an environmentally acceptable and cost-effective strategy for synthesizing highly functionalized organic molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"108 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846674","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
Decatungstate-Catalyzed Hydrosilylation of α-Trifluoromethylalkenes for Construction of α-Trifluoromethyl-β-silanes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-18 DOI: 10.1021/acs.orglett.5c00796
Rui Xiao, Yutong Lang, Ziqiang Cheng, Liejin Zhou, Zhong-Yan Cao, Zheliang Yuan, Yanan Wang
{"title":"Decatungstate-Catalyzed Hydrosilylation of α-Trifluoromethylalkenes for Construction of α-Trifluoromethyl-β-silanes","authors":"Rui Xiao, Yutong Lang, Ziqiang Cheng, Liejin Zhou, Zhong-Yan Cao, Zheliang Yuan, Yanan Wang","doi":"10.1021/acs.orglett.5c00796","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00796","url":null,"abstract":"The hydrosilylation of alkenes is a pivotal transformation for the synthesis of organosilanes; however, the hydrosilylation of fluorine-containing alkenes is limited due to the facile β-fluoride elimination. Herein, by employing the direct hydrogen atom transfer (HAT) catalyst, tetrabutylammonium decatungstate (TBADT), and using disulfide as a co-catalyst, we have successfully developed a mild photocatalytic hydrosilylation of α-trifluoromethylalkenes for the synthesis of α-trifluoromethyl-β-silanes. Our method features mild conditions, good regioselectivity, and compatibility. The β-fluoride elimination was fully inhibited. A radical mechanism was proposed based on the preliminary results.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"4 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846676","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
Electrochemical Deaminative Carboxylation of Aryltriazenes with CO2 to Aryl Carboxylic Acids
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-04-18 DOI: 10.1021/acs.orglett.5c01099
Lan Zhao, An-Guo Wu, Hong-Ru Li, Alexander O. Terent’ev, Liang-Nian He
{"title":"Electrochemical Deaminative Carboxylation of Aryltriazenes with CO2 to Aryl Carboxylic Acids","authors":"Lan Zhao, An-Guo Wu, Hong-Ru Li, Alexander O. Terent’ev, Liang-Nian He","doi":"10.1021/acs.orglett.5c01099","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c01099","url":null,"abstract":"The utilization of CO<sub>2</sub> as an appealing chemical feedstock for diverse synthetically valuable products is constantly evolving, potentially alleviating chemical production that relies on petrochemistry. Herein we report the first example of the electrochemical deaminative carboxylation of aryltriazenes with CO<sub>2</sub>. The reaction can be performed under mild and catalyst-free conditions by using sustainable methods with CO<sub>2</sub> as a green C<sub>1</sub> building block, efficiently converting a diverse range of readily available aryltriazenes into synthetically valuable carboxylic acids. In particular, the formation of C–C bonds by deaminative carboxylation would be an impactful addition to the synthesis toolbox.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"8 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846679","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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