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Machine learning-guided strategies for reaction conditions design and optimization. 以机器学习为指导的反应条件设计和优化策略。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-04 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.212
Lung-Yi Chen, Yi-Pei Li
{"title":"Machine learning-guided strategies for reaction conditions design and optimization.","authors":"Lung-Yi Chen, Yi-Pei Li","doi":"10.3762/bjoc.20.212","DOIUrl":"https://doi.org/10.3762/bjoc.20.212","url":null,"abstract":"<p><p>This review surveys the recent advances and challenges in predicting and optimizing reaction conditions using machine learning techniques. The paper emphasizes the importance of acquiring and processing large and diverse datasets of chemical reactions, and the use of both global and local models to guide the design of synthetic processes. Global models exploit the information from comprehensive databases to suggest general reaction conditions for new reactions, while local models fine-tune the specific parameters for a given reaction family to improve yield and selectivity. The paper also identifies the current limitations and opportunities in this field, such as the data quality and availability, and the integration of high-throughput experimentation. The paper demonstrates how the combination of chemical engineering, data science, and ML algorithms can enhance the efficiency and effectiveness of reaction conditions design, and enable novel discoveries in synthetic chemistry.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2476-2492"},"PeriodicalIF":2.2,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457048/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387569","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
HFIP as a versatile solvent in resorcin[n]arene synthesis. HFIP 作为合成间苯二酚[n]炔的多功能溶剂。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-02 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.211
Hormoz Khosravi, Valeria Stevens, Raúl Hernández Sánchez
{"title":"HFIP as a versatile solvent in resorcin[<i>n</i>]arene synthesis.","authors":"Hormoz Khosravi, Valeria Stevens, Raúl Hernández Sánchez","doi":"10.3762/bjoc.20.211","DOIUrl":"https://doi.org/10.3762/bjoc.20.211","url":null,"abstract":"<p><p>Herein, we present 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as an efficient solvent for synthesizing resorcin[<i>n</i>]arenes in the presence of catalytic amounts of HCl at ambient temperature and within minutes. Remarkably, resorcinols with electron-withdrawing groups and halogens, which are reported in the literature as the most challenging precursors in this cyclization, are tolerated. This method leads to a variety of 2-substituted resorcin[<i>n</i>]arenes in a single synthetic step with isolated yields up to 98%.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2469-2475"},"PeriodicalIF":2.2,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457071/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387567","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams. 光氧化催化烯与β-内酰胺的分子内亲核酰胺化反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-01 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.210
Valentina Giraldi, Giandomenico Magagnano, Daria Giacomini, Pier Giorgio Cozzi, Andrea Gualandi
{"title":"Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams.","authors":"Valentina Giraldi, Giandomenico Magagnano, Daria Giacomini, Pier Giorgio Cozzi, Andrea Gualandi","doi":"10.3762/bjoc.20.210","DOIUrl":"https://doi.org/10.3762/bjoc.20.210","url":null,"abstract":"<p><p>The direct nucleophilic addition of amides to unfunctionalized alkenes via photoredox catalysis represents a facile approach towards functionalized alkylamides. Unfortunately, the scarce nucleophilicity of amides and competitive side reactions limit the utility of this approach. Herein, we report an intramolecular photoredox cyclization of alkenes with β-lactams in the presence of an acridinium photocatalyst. The approach uses an intramolecular nucleophilic addition of the β-lactam nitrogen atom to the radical cation photogenerated in the linked alkene moiety, followed by hydrogen transfer from the hydrogen atom transfer (HAT) catalyst. This process was used to successfully prepare 2-alkylated clavam derivatives.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2461-2468"},"PeriodicalIF":2.2,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457124/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387570","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols. 高价碘介导的双烯丙基酰胺环化生成脯氨醇。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-30 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.209
Smaher E Butt, Konrad Kepski, Jean-Marc Sotiropoulos, Wesley J Moran
{"title":"Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols.","authors":"Smaher E Butt, Konrad Kepski, Jean-Marc Sotiropoulos, Wesley J Moran","doi":"10.3762/bjoc.20.209","DOIUrl":"https://doi.org/10.3762/bjoc.20.209","url":null,"abstract":"<p><p>A change in mechanism was observed in the hypervalent iodine-mediated cyclization of <i>N</i>-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to form the pyrrolidine ring was favored over cyclization at the amide oxygen. A DFT study was undertaken to rationalize the change in mechanism of this cyclization process. In addition, reaction conditions were developed, and the scope of this cyclization studied.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2455-2460"},"PeriodicalIF":2.2,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457059/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387568","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose. ᴅ-塔罗糖吡喃间卤化物类似物的合成和构象分析。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-27 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.208
Olivier Lessard, Mathilde Grosset-Magagne, Paul A Johnson, Denis Giguère
{"title":"Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose.","authors":"Olivier Lessard, Mathilde Grosset-Magagne, Paul A Johnson, Denis Giguère","doi":"10.3762/bjoc.20.208","DOIUrl":"10.3762/bjoc.20.208","url":null,"abstract":"<p><p>In this work, we describe the synthesis of halogenated pyran analogues of ᴅ-talose using a halo-divergent strategy from known 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-ᴅ-mannopyranose. In solution and in the solid-state, all analogues adopt standard <sup>4</sup> <i>C</i> <sub>1</sub>-like conformations despite 1,3-diaxial repulsion between the F2 and the C4 halogen. Moreover, the solid-state conformational analysis of halogenated pyrans reveals deviation in the intra-annular torsion angles arising from repulsion between the axial fluorine at C2 and the axial halogen at C4, which increases with the size of the halogen at C4 (F < Cl < Br < I). Crystal packing arrangements of pyran inter-halides show hydrogen bond acceptor and nonbonding interactions for the halogen at C4. Finally, density functional theory (DFT) calculations corroborate the preference of talose analogues to adopt a <sup>4</sup> <i>C</i> <sub>1</sub>-like conformation and a natural bonding orbital (NBO) analysis demonstrates the effects of hyperconjugation from C-F antibonding orbitals.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2442-2454"},"PeriodicalIF":2.2,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443651/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Phenylseleno trifluoromethoxylation of alkenes. 烯烃的苯基硒三氟甲氧基化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-26 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.207
Clément Delobel, Armen Panossian, Gilles Hanquet, Frédéric R Leroux, Fabien Toulgoat, Thierry Billard
{"title":"Phenylseleno trifluoromethoxylation of alkenes.","authors":"Clément Delobel, Armen Panossian, Gilles Hanquet, Frédéric R Leroux, Fabien Toulgoat, Thierry Billard","doi":"10.3762/bjoc.20.207","DOIUrl":"10.3762/bjoc.20.207","url":null,"abstract":"<p><p>Trifluoromethoxylated molecules and selenylated compounds find a wide range of interesting applications, but separately. In order to combine the potential of these two motifs and to propose a new class of compounds, we have developed an electrophilic phenylseleno trifluoromethoxylation of alkenes, which leads to β-selenylated trifluoromethoxylated compounds or, upon subsequent reduction, to the trifluoromethoxylated ones.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2434-2441"},"PeriodicalIF":2.2,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443662/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360894","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles. 简便制备含氟 2,3-环氧丙酸酯及其与各种亲核物的环氧开环反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-25 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.206
Yutaro Miyashita, Sae Someya, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Takashi Yamazaki
{"title":"Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles.","authors":"Yutaro Miyashita, Sae Someya, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Takashi Yamazaki","doi":"10.3762/bjoc.20.206","DOIUrl":"10.3762/bjoc.20.206","url":null,"abstract":"<p><p>We describe herein a facile method to access 2,3-epoxyesters with fluorine-containing substituents at their 3-position starting from the corresponding enoates by utilization of the low-costed and easy-to-handle reagent, NaOCl·5H<sub>2</sub>O. Because very little has been disclosed about the reactivity of such 2,3-epoxyesters, their epoxy ring opening by a variety of nucleophiles was carried out and we succeeded in clarifying these chemo- as well as regioselective processes proceeding via the S<sub>N</sub>2 mechanism to mainly afford 2-substituted 3-hydroxyesters usually in a highly <i>anti</i> selective manner.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2421-2433"},"PeriodicalIF":2.2,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443650/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360893","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Homogeneous continuous flow nitration of O-methylisouronium sulfate and its optimization by kinetic modeling. O-甲基异脲硫酸盐的均相连续流硝化及其动力学模型优化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-24 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.205
Jiapeng Guo, Weike Su, An Su
{"title":"Homogeneous continuous flow nitration of <i>O</i>-methylisouronium sulfate and its optimization by kinetic modeling.","authors":"Jiapeng Guo, Weike Su, An Su","doi":"10.3762/bjoc.20.205","DOIUrl":"10.3762/bjoc.20.205","url":null,"abstract":"<p><p>Nitration of <i>O</i>-methylisouronium sulfate under mixed acid conditions gives <i>O</i>-methyl-<i>N</i>-nitroisourea, a key intermediate of neonicotinoid insecticides with high application value. The reaction is a fast and highly exothermic process with a high mass transfer resistance, making its control difficult and risky. In this paper, a homogeneous continuous flow microreactor system was developed for the nitration of <i>O</i>-methylisouronium sulfate under high concentrations of mixed acids, with a homemade static mixer eliminating the mass transfer resistance. In addition, the kinetic modeling of this reaction was performed based on the theory of NO<sub>2</sub> <sup>+</sup> attack, with the activation energy and pre-exponential factor determined. Finally, based on the response surface generated by the kinetic model, the reaction was optimized with a conversion of 87.4% under a sulfuric acid mass fraction of 94%, initial reactant concentration of 0.5 mol/L, reaction temperature of 40 °C, molar ratio of reactants at 4.4:1, and a residence time of 12.36 minutes.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2408-2420"},"PeriodicalIF":2.2,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11445654/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142368181","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt. 评估碘异噁唑鎓（III）盐的卤素键强度。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-23 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.204
Dominik L Reinhard, Anna Schmidt, Marc Sons, Julian Wolf, Elric Engelage, Stefan M Huber
{"title":"Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt.","authors":"Dominik L Reinhard, Anna Schmidt, Marc Sons, Julian Wolf, Elric Engelage, Stefan M Huber","doi":"10.3762/bjoc.20.204","DOIUrl":"10.3762/bjoc.20.204","url":null,"abstract":"<p><p>Diaryliodonium(III) salts have been established as powerful halogen-bond donors in recent years. Herein, a new structural motif for this compound class was developed: iodoloisoxazolium salts, bearing a cyclic five-membered iodolium core fused with an isoxazole ring. A derivative of this class was synthesized and investigated in the solid state by X-ray crystallography. Finally, the potential as halogen-bonding activator was benchmarked in solution in the gold-catalyzed cyclization of a propargyl amide.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2401-2407"},"PeriodicalIF":2.2,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11443664/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360892","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO. 在二甲基亚砜中通过电化学方法直接羧化二芳基甲醇化合物，一步法高效合成二芳基乙酸。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-20 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.203
Hisanori Senboku, Mizuki Hayama
{"title":"Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO.","authors":"Hisanori Senboku, Mizuki Hayama","doi":"10.3762/bjoc.20.203","DOIUrl":"https://doi.org/10.3762/bjoc.20.203","url":null,"abstract":"<p><p>An efficient one-step synthesis of diarylacetic acids was successfully performed by electrochemical direct carboxylation of diarylmethanol compounds in DMSO. Constant-current electrolysis of diarylmethanol species in DMSO using a one-compartment cell equipped with a Pt cathode and a Mg anode in the presence of carbon dioxide induced reductive C(sp<sup>3</sup>)-O bond cleavage at the benzylic position in diarylmethanol compounds and subsequent fixation of carbon dioxide to produce diarylacetic acids in good yield. This protocol provides a novel and simple approach to diarylacetic acids from diarylmethanol species and carbon dioxide without transformation of the hydroxy group into appropriate leaving groups, such as halides and esters including carbonates.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2392-2400"},"PeriodicalIF":2.2,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11420549/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142340300","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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