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Directing Group Assisted Transition Metal Catalyzed Selective BH Functionalization of o-Carboranes 定向基团辅助过渡金属催化邻碳硼烷的选择性 BH 功能化
Synthesis Pub Date : 2024-06-11 DOI: 10.1055/a-2343-0780
Jie Zhang, Zuowei Xie
{"title":"Directing Group Assisted Transition Metal Catalyzed Selective BH Functionalization of o-Carboranes","authors":"Jie Zhang, Zuowei Xie","doi":"10.1055/a-2343-0780","DOIUrl":"https://doi.org/10.1055/a-2343-0780","url":null,"abstract":"Carboranes are a type of molecular clusters consisting of carbon, hydrogen and boron atoms. They possess unique characteristics such as three-dimensional aromaticity, icosahedral geometry, and robustness. Functionalized carboranes have been utilized in various fields including medicine, materials, and organometallic/coordination chemistry. In this context, selective functionalization of o-carboranes has received tremendous attention, specifically in the regio- and enantio-selective modification of the ten chemically similar BH vertices within the carborane cage. In recent years, significant progress has been made in catalytic vertex-specific BH functionalization, as well as achieving enantioselective functionalization of the cage BH. This review provides an overview of the recent advancements in this research field.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141360333","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
Palladium-Catalyzed Amino-Sulfonylation of Aryl Iodide Derivatives via the Insertion of Sulfur Dioxide: One-Pot Synthesis of Aryl Primary Sulfonamides with Thiourea Dioxides 钯催化下通过插入二氧化硫对芳基碘化物衍生物进行氨基磺化反应：芳基伯磺酰胺与硫脲二氧杂环的一步法合成
Synthesis Pub Date : 2024-06-10 DOI: 10.1055/s-0040-1720112
Panyu Ge, Ziyi Zhou, Jiahao Tao, Wei Cai, Minqin Wu, Xinggang Shan, Yong Li, Kai Cheng
{"title":"Palladium-Catalyzed Amino-Sulfonylation of Aryl Iodide Derivatives via the Insertion of Sulfur Dioxide: One-Pot Synthesis of Aryl Primary Sulfonamides with Thiourea Dioxides","authors":"Panyu Ge, Ziyi Zhou, Jiahao Tao, Wei Cai, Minqin Wu, Xinggang Shan, Yong Li, Kai Cheng","doi":"10.1055/s-0040-1720112","DOIUrl":"https://doi.org/10.1055/s-0040-1720112","url":null,"abstract":"<p>A palladium-catalyzed one-pot amino-sulfonylation of aryl iodide derivatives with thiourea dioxide, PdCl<sub>2</sub>dppf, and one-pot added hydroxylamine-<i>O</i>-sulfonic acid is presented. This amino-sulfonylation gave structure diversity to aryl primary sulfonamides and features good functional group compatibility, mild reaction conditions, excellent regioselectivity, and moderate to good yields. The robustness and potential of this method have also been successfully demonstrated by late-stage elaboration and gram-scale reaction. This approach achieves the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as Sulpiride, Venetoclax, and Furosemide­.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528666","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
Progress on the Synthesis and Applications of Aminals: Scaffolds for Molecular Diversity Aminals 的合成和应用进展：分子多样性的支架
Synthesis Pub Date : 2024-06-10 DOI: 10.1055/a-2317-6604
Rafael Rippel, Luísa M. Ferreira, Paula S. Branco
{"title":"Progress on the Synthesis and Applications of Aminals: Scaffolds for Molecular Diversity","authors":"Rafael Rippel, Luísa M. Ferreira, Paula S. Branco","doi":"10.1055/a-2317-6604","DOIUrl":"https://doi.org/10.1055/a-2317-6604","url":null,"abstract":"<p>Aminals, characterized by a central carbon linking two nitrogen atoms, are versatile building blocks in modern chemistry. This review addresses a literature gap by exploring the synthesis and applications of aminals, with a focus on drug discovery and molecular diversity. Beyond medicinal chemistry, aminals find applications as key components in bioactive compounds and as versatile tools in materials chemistry. The review covers fundamental characteristics, synthetic methodologies, stability, and applications, emphasizing alternative synthetic methods to the well-established aldehyde–amine condensation. This inclusive exploration provides insights into diverse synthetic pathways that expand the versatility of the aminal scaffold.</p> <p>1 Introduction</p> <p>2 The Aminal Group</p> <p>3 Aminal Synthesis</p> <p>3.1 Metal-Free Approaches</p> <p>3.2 Metal-Catalyzed Approaches</p> <p>3.3 Photoredox Methodologies</p> <p>3.4 Via Rearrangements</p> <p>3.5 Via Decarboxylative Coupling</p> <p>4 Aminals as Synthetic Tools</p> <p>5 Synthesis of Aminal-Containing Natural Products</p> <p>6 Aminal-Based Materials</p> <p>7 Conclusions</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528665","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
Chemical Synthesis of a Disaccharide from Vibrio vulnificus Biotype 2 Serovar A O-antigen Containing a Rare L-GalpNAmA 弧菌 Biotype 2 Serovar A O 抗原二糖的化学合成，其中含有罕见的 L-GalpNAmA
Synthesis Pub Date : 2024-06-07 DOI: 10.1055/a-2341-3462
Shengyong Zhu, Jing Hu, Qingjun You, Guangzong Tian, Xiaopeng Zou, Chunjun Qin, Jian Yin
{"title":"Chemical Synthesis of a Disaccharide from Vibrio vulnificus Biotype 2 Serovar A O-antigen Containing a Rare L-GalpNAmA","authors":"Shengyong Zhu, Jing Hu, Qingjun You, Guangzong Tian, Xiaopeng Zou, Chunjun Qin, Jian Yin","doi":"10.1055/a-2341-3462","DOIUrl":"https://doi.org/10.1055/a-2341-3462","url":null,"abstract":"Vibrio vulnificus can cause severe infections internally and externally. The mortality rate of V. vulnificus-associated gangrene and septicemia has increased due to antibiotic resistance and the absence of human vaccine. Bacterial carbohydrates have been widely used in the development of bacterial vaccines. Here, a rare L-GalpNAmA-containing disaccharide exists in V. vulnificus biotype 2 serovar A O-antigen was synthesized from D-glucose and L-galactose. An investigation on the influence of different linkers on the disaccharide synthetic efficiency indicated that the amine linker has more practicality. Two α-glycosidic linkages were constructed with good stereoselectivity by using nonparticipating C2 azido group and solvent effect. An orthogonal protection strategy allowed introductions of carboxyl and acetamidino (Am) groups at the disaccharide stage. The synthesis of the amine-linked disaccharide will provide a basis for the preparation of the trisaccharide repeating unit and longer fragments of V. vulnificus biotype 2 serovar A O-antigen, as well as other complex glycans.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141373671","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
Iron-Mediated Bromocyclization of Olefinic Amides for the Synthesis of Bromobenzoxazines 铁介导的烯烃酰胺溴环化反应用于合成溴苯并噁嗪
Synthesis Pub Date : 2024-06-05 DOI: 10.1055/a-2338-8479
Da‐Zhen Xu, Tong-Tong Zhao, Qiang Bian, Yu-Wei Zhao, Lin-Lin Xu, Wei-Guang Zhao
{"title":"Iron-Mediated Bromocyclization of Olefinic Amides for the Synthesis of Bromobenzoxazines","authors":"Da‐Zhen Xu, Tong-Tong Zhao, Qiang Bian, Yu-Wei Zhao, Lin-Lin Xu, Wei-Guang Zhao","doi":"10.1055/a-2338-8479","DOIUrl":"https://doi.org/10.1055/a-2338-8479","url":null,"abstract":"An iron-mediated bromination/cyclization for the synthesis of bromobenzoxazines from olefinic amides has been successfully developed. In this protocol, the simple iron salt FeBr3 was employed as a bromination reagent, giving the bromobenzoxazine products in moderate to excellent yields. This methodology features good functional group tolerance, gram-scale synthesis and green reaction conditions by the use of air as the terminal oxidant. Preliminary mechanistic studies suggest that a free radical pathway is involved.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141381998","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
Tandem [5,5]-/[3,3]- rearrangements of aryl sulfoxides with allyl nitriles 芳基硫醚与烯丙基腈的串联[5,5]-/[3,3]-重排反应
Synthesis Pub Date : 2024-06-05 DOI: 10.1055/a-2338-9005
Mengjie Hu, Liying Ru, Mengjiao Zhu, Shengwen Yang, Suojiang Fan, Jiangtao Ji, Dingming Zheng, Bo Peng
{"title":"Tandem [5,5]-/[3,3]- rearrangements of aryl sulfoxides with allyl nitriles","authors":"Mengjie Hu, Liying Ru, Mengjiao Zhu, Shengwen Yang, Suojiang Fan, Jiangtao Ji, Dingming Zheng, Bo Peng","doi":"10.1055/a-2338-9005","DOIUrl":"https://doi.org/10.1055/a-2338-9005","url":null,"abstract":"Tandem aromatic rearrangements can redirect the regioselectivity of original rearrangement and increase the complexity of products. Despite their obvious synthetic value, only few protocols of tandem aromatic rearrangements are reported. In this Article, we describe two new tandem aromatic rearrangements by using sulfonium rearrangements. Specifically, [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles followed by [3,3]-Cope rearrangement forges the tandem [5,5]-/[3,3]-rearrangements which affords ortho-functionalized phenyl sulfides as products. The other tandem rearrangement proceeds through [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles and the subsequent nuclephilic addition/DDQ-oxidation induced [3,3]-Cope rearrangement, which eventually achieves meta-functionalized phenyl sulfides as products.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141384305","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
Photoinduced Aryl Ketone-Catalyzed Phenylation of C(sp3)–H Bonds Attached to the Heteroatom of Ethers and N-Boc-amines via Concerted Homolytic Aromatic Substitution 光诱导芳基酮通过协同同溶芳香族取代催化醚和 N-叔丁氧羰基胺杂原子上的 C（sp3）-H 键的苯化作用
Synthesis Pub Date : 2024-06-04 DOI: 10.1055/a-2338-4243
Masaya Azami, Michinori Sumimoto, Reika Nakamura, T. Murafuji, Shin Kamijo
{"title":"Photoinduced Aryl Ketone-Catalyzed Phenylation of C(sp3)–H Bonds Attached to the Heteroatom of Ethers and N-Boc-amines via Concerted Homolytic Aromatic Substitution","authors":"Masaya Azami, Michinori Sumimoto, Reika Nakamura, T. Murafuji, Shin Kamijo","doi":"10.1055/a-2338-4243","DOIUrl":"https://doi.org/10.1055/a-2338-4243","url":null,"abstract":"A single-step phenylation at the non-acidic C(sp3)–H bond attached to the heteroatom of ethers and N-Boc-amines has been achieved using photoexcited 4-benzoylpyridine as a hydrogen atom transfer (HAT) catalyst. The design of electron-deficient (trifluoromethylsulfonyl)benzene derivatives, as a phenyl precursor, was critical to realizing the present transformation. Moreover, the DFT calculation indicated that the present transformation proceeds via a concerted homolytic aromatic substitution rather than via a stepwise one involving the formation of a cyclohexadienyl radical intermediate.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141267179","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
Diastereo-Divergent Synthesis of Ring A-lactones Derived From Cholesterol and Diosgenin. A Convenient Solution for an Old Problem. NMR and X-Ray Characterization 胆固醇和薯蓣皂苷衍生环 A-内酯的非对映-歧化合成。老问题的便捷解决方案。核磁共振和 X 射线表征
Synthesis Pub Date : 2024-06-04 DOI: 10.1055/a-2338-4149
William H. García‐Santos, Paola Valente-Valdovinos, Alvaro J. Cortina-Mendoza, Marcos FLORES-ALAMOS, M. A. Iglesias‐Arteaga
{"title":"Diastereo-Divergent Synthesis of Ring A-lactones Derived From Cholesterol and Diosgenin. A Convenient Solution for an Old Problem. NMR and X-Ray Characterization","authors":"William H. García‐Santos, Paola Valente-Valdovinos, Alvaro J. Cortina-Mendoza, Marcos FLORES-ALAMOS, M. A. Iglesias‐Arteaga","doi":"10.1055/a-2338-4149","DOIUrl":"https://doi.org/10.1055/a-2338-4149","url":null,"abstract":"A convenient protocol for the synthesis of A-ring lactones derived from cholesterol was developed. A lactone reduction-lactol separation-reoxidation sequence, applied to the inseparable mixture of diastereomeric lactones allows the production of multigram amounts of each lactone in pure form. The same sequence applied to A-ring lactones derived from diosgenin produced similar results. A detailed NMR characterization of all the obtained lactones is also provided. X-ray diffraction corroborated the structure of the obtained compounds.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141268541","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 Total Synthesis of Lobophopyranone A and B Lobophopyranone A 和 B 的不对称全合成
Synthesis Pub Date : 2024-06-04 DOI: 10.1055/a-2338-4462
D. Mohapatra, Sudhakar Reddy Guvvala, U. Choudhury, Sai Keerthana Haritha, Karamtothu Charan Naik
{"title":"Asymmetric Total Synthesis of Lobophopyranone A and B","authors":"D. Mohapatra, Sudhakar Reddy Guvvala, U. Choudhury, Sai Keerthana Haritha, Karamtothu Charan Naik","doi":"10.1055/a-2338-4462","DOIUrl":"https://doi.org/10.1055/a-2338-4462","url":null,"abstract":"The first asymmetric total synthesis and structural confirmation of lobophopyranone A and B have been accomplished from commercially available starting materials. Reagent-controlled Keck-Maruoka allylation, Grignard reaction, chelation-controlled Sakurai allylation, and acid-mediated one-step TBS ether deprotection followed by cyclization are the crucial stages in this synthesis that create the 2,6-disubstituted dihydropyranone component.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141267625","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
Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Iso­cyanide as CO Equivalent Leading to 1,2-Diketones 可回收钯催化芳基卤化物和有机铝化合物与叔丁基异氰酸酯的羰基偶联反应，生成 1,2-二酮类化合物
Synthesis Pub Date : 2024-06-03 DOI: 10.1055/s-0040-1720121
Zhiyuan Tu, Jianan Zhan, Shengyong You, Mingzhong Cai
{"title":"Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Iso­cyanide as CO Equivalent Leading to 1,2-Diketones","authors":"Zhiyuan Tu, Jianan Zhan, Shengyong You, Mingzhong Cai","doi":"10.1055/s-0040-1720121","DOIUrl":"https://doi.org/10.1055/s-0040-1720121","url":null,"abstract":"<p>An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using <i>tert</i>-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KO<sup>t</sup>Bu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141254786","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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