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Photocatalytic C-I Bond Borylation and Phosphorylation of Diaryliodonium Salts with Excellent Atom-Economy 具有优异原子经济性的二芳基碘鎓盐的光催化C-I键硼化和磷酸化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-09 DOI: 10.1002/adsc.202401240
Tian-Yu Ding, Xiao-Ning Guo, Bin Chen, Chen-Ho Tung, Li-Zhu Wu
{"title":"Photocatalytic C-I Bond Borylation and Phosphorylation of Diaryliodonium Salts with Excellent Atom-Economy","authors":"Tian-Yu Ding, Xiao-Ning Guo, Bin Chen, Chen-Ho Tung, Li-Zhu Wu","doi":"10.1002/adsc.202401240","DOIUrl":"https://doi.org/10.1002/adsc.202401240","url":null,"abstract":"Highly atom-economic conversion of diaryliodonium salts represents an underdeveloped but highly desirable domain. Most reactions involving these species only utilize single aryl group of the diaryliodonium and produce an equivalent of aryl iodide as waste. Herein, by further transforming the side-product aryl iodide, we report an overall new two-step one-pot strategy that allows photocatalytic C−I bond borylation and phosphorylation of diaryliodonium salts and ensures effective conversion of both aryl groups of the diaryliodonium into the relevant arylboronic esters or arylphosphonic esters. Mechanistic investigations suggest that electron-donor-acceptor (EDA) complex is formed between the photocatalyst phenothiazine (PTH) and diaryliodonium salt substrate. Upon visible light irradiation, this complex produces aryl radical and aryl iodide. With addition of a base in the second step, the reducing ability of the photocatalyst is enhanced via proton-coupled electron transfer (PCET) process, thereby aryl iodide produced in the first step is reduced to yield aryl radical again. Both aryl radicals generated in the two steps react with B2(OR)4 or P(OR)3 to produce the corresponding monoarylation product in a quantitative yield.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797653","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Stereoselective Synthesis of Aliphatic α-Amino Acids by Chemo-Enzymatic Hydroamination-Hydrodesulfurisation 化学-酶加氢胺-加氢脱硫法立体选择性合成脂肪族α-氨基酸
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-08 DOI: 10.1002/adsc.202401223
Celeste Nobbio, William R. Birmingham, Elisabetta Brenna, Nicholas J. Turner, Davide Tessaro, Fabio Parmeggiani
{"title":"Stereoselective Synthesis of Aliphatic α-Amino Acids by Chemo-Enzymatic Hydroamination-Hydrodesulfurisation","authors":"Celeste Nobbio, William R. Birmingham, Elisabetta Brenna, Nicholas J. Turner, Davide Tessaro, Fabio Parmeggiani","doi":"10.1002/adsc.202401223","DOIUrl":"https://doi.org/10.1002/adsc.202401223","url":null,"abstract":"Phenylalanine ammonia lyase (PAL) enzymes have been extensively exploited to produce differently substituted arylalanine analogues, but their use in the stereoselective synthesis of aliphatic fatty amino acids has never been addressed. In this work, a two-step hydroamination-hydrodesulfurisation process has been investigated for the production of aliphatic L-α-amino acids from thienylacrylic acids, easily accessible by condensation from the corresponding arylaldehyde. Wild-type PALs from Planctomyces brasiliensis and Streptomyces rimosus were selected as the most promising candidates and improved by site-directed mutagenesis, thus unlocking the hydroamination of a broad panel of 10 different thienylacrylic acids bearing aliphatic and aromatic substituents. The subsequent hydrodesulfurisation step, accomplished by means of inexpensive Raney nickel in mild conditions and aqueous medium, afforded the corresponding aliphatic α-amino acids in 10-63% overall isolated yield and perfect enantiopurity. This chemo-enzymatic process represents the first example of aliphatic amino acid production using PALs, circumventing a major limitation of those biocatalysts.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"28 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Chemo- and Enantioselective Intermolecular Allylation of Quinolin-2-ones 喹啉-2- 1的化学和对映选择性分子间烯丙基化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-08 DOI: 10.1002/adsc.202401113
Zihao Li, Yumeng Wang, Yuqiao Zhou, Zongli Xiong, Jian Wang, Weijun Yao, Zhen Wang
{"title":"Chemo- and Enantioselective Intermolecular Allylation of Quinolin-2-ones","authors":"Zihao Li, Yumeng Wang, Yuqiao Zhou, Zongli Xiong, Jian Wang, Weijun Yao, Zhen Wang","doi":"10.1002/adsc.202401113","DOIUrl":"https://doi.org/10.1002/adsc.202401113","url":null,"abstract":"An enantioselective C-, O- and N- intermolecular allylic reaction of quinolin-2(1H)-ones has been developed. The reaction between 3-hydroxy quinolone and Boc-protected MBH adducts with Pd-catalysis provided a series of 1,4-dihydroquinoline-2,3-diones in 20-95% yield accompanied by 69-96% enantioselectivity. In addition, the O-allylic alkylation could occur by varying the organo-catalyst and Boc-protected MBH adducts from benzaldehyde. Furthermore, the N-allylation of 3-O-protected quinolin-2-ones with allylic acetates was also realized (40-92% yield, 78-97% ee).","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"115 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793798","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Temperature-Controlled Dearomative [5+1] Spiroannulation and Formal [5+2] Cyclization of Indoles with Enynones: Divergent Synthesis of Spiro-Indolenines and Dihydrocyclohepta[b]Indolones 吲哚与烯酮的温控脱芳[5+1]螺旋环化和正构[5+2]环化：螺旋-吲哚啉和二氢环庚的歧化法合成[j]
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-08 DOI: 10.1002/adsc.202401072
Bin Dong, Zhiming Li, Wei Li, Jiang Deng, Junyuan Yan, Yihan Guo, Kai-Kai Wang, Shan Qian, Zhouyu Wang, Xiao-Long He
{"title":"Temperature-Controlled Dearomative [5+1] Spiroannulation and Formal [5+2] Cyclization of Indoles with Enynones: Divergent Synthesis of Spiro-Indolenines and Dihydrocyclohepta[b]Indolones","authors":"Bin Dong, Zhiming Li, Wei Li, Jiang Deng, Junyuan Yan, Yihan Guo, Kai-Kai Wang, Shan Qian, Zhouyu Wang, Xiao-Long He","doi":"10.1002/adsc.202401072","DOIUrl":"https://doi.org/10.1002/adsc.202401072","url":null,"abstract":"<p>We developed a temperature-controlled intermolecular dearomative [5+1] spiroannulation and [5+2] cyclization of indoles with enynones, smoothly delivering a variety of spiroindolenines and dihydrocyclohepta[<i>b</i>]indolones under 40 °C and 80 °C, respectively. A three-step cascade reaction was also realized by using OTBS or NHBoc containing enynones in the reaction with the indole under the identical condition. And a novel valuable highly-oriented three-dimensional indole-based tetracyclic scaffold was produced in high yields with excellent diastereoselectivities. Additionally, various spiroindolines and spirooxindoles were facilely produced through simple operations. This highly efficient domino-reaction represents an emblematic method for the preparation of indole-based polycycles through the intermolecular pathway.</p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"9 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793797","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Metal‐free visible‐light‐induced direct synthesis of alkyl‐substituted phosphonodithioates from white phosphorus (P4) 无金属可见光诱导白磷直接合成烷基取代膦二硫代酸盐（P4）
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-07 DOI: 10.1002/adsc.202401355
Fengxiao Wang, Xiyuan Zhang, Jiaming Xu, Qitao Shen, Bo Jiang, Zhiwei Miao
{"title":"Metal‐free visible‐light‐induced direct synthesis of alkyl‐substituted phosphonodithioates from white phosphorus (P4)","authors":"Fengxiao Wang, Xiyuan Zhang, Jiaming Xu, Qitao Shen, Bo Jiang, Zhiwei Miao","doi":"10.1002/adsc.202401355","DOIUrl":"https://doi.org/10.1002/adsc.202401355","url":null,"abstract":"The direct synthesis of organic phosphorus compounds from white phosphorus (P4) is a longstanding challenge in organic synthesis. Here, we present a novel visible light‐induced three‐component functionalization reaction that integrates P4, disulfide compounds, and N‐hydroxyphthalimide (NHPI) esters to produce alkyl‐substituted phosphonodithioates in a one‐pot process. Using 2,4,5,6‐tetrakis(carbazol‐9‐yl)‐1,3‐dicyanobenzene (4CzIPN) as a photocatalyst, blue LEDs (456 nm) as the light source, and N,N‐diisopropylethylamine (DIPEA) as the reducing agent in an acetone‐toluene solvent system, this method achieves moderate to good yields of structurally diverse phosphonodithioates. The reaction proceeds under mild conditions, ensures complete conversion of P4, avoids chlorination, and uses inexpensive, readily available starting materials, offering potential for large‐scale applications.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"221 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142788446","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Regioselective Cobalt‐Catalyzed Protoboration of Alkynes 区域选择性钴催化炔的原硼化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-06 DOI: 10.1002/adsc.202401334
Ho Seong Hwang, Eun Jin Cho
{"title":"Regioselective Cobalt‐Catalyzed Protoboration of Alkynes","authors":"Ho Seong Hwang, Eun Jin Cho","doi":"10.1002/adsc.202401334","DOIUrl":"https://doi.org/10.1002/adsc.202401334","url":null,"abstract":"A regioselective cobalt‐catalyzed protoboration of alkynes has been developed, utilizing diboron as the borylation source for the efficient synthesis of alkenylborates. The reaction proceeds via cobalt‐boryl intermediates, diverging from conventional Co‐H chemistry. By fine‐tuning the phosphine ligand side chains, we achieved excellent reactivity and regioselectivity across a wide range of internal and terminal alkynes. This Co‐catalyzed method offers significant advantages in terms of both efficiency and environmental impact, making it an attractive approach for the synthesis of complex organic molecules.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"3 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142782814","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Regiospecific Alkene Oxyamination via N‐Alkylation‐Hydroxylation‐Transesterification Cascades 通过N -烷基化-羟基化-酯交换级联反应的区域特异性烯烃氧化胺化
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-06 DOI: 10.1002/adsc.202401365
Hong-Xia Zhang, Li-Gang Kou, Ya-Ru Gao, Qiong Jia, Yong-Qiang Wang
{"title":"Regiospecific Alkene Oxyamination via N‐Alkylation‐Hydroxylation‐Transesterification Cascades","authors":"Hong-Xia Zhang, Li-Gang Kou, Ya-Ru Gao, Qiong Jia, Yong-Qiang Wang","doi":"10.1002/adsc.202401365","DOIUrl":"https://doi.org/10.1002/adsc.202401365","url":null,"abstract":"An unprecedented cascade reaction of simple inactive alkenes, azo compounds and H2O to produce valuable poly‐substituted oxazolidinones is reported herein. The transformation possesses exclusive regioselectivity, and features mild reaction conditions and a broad substrate scope. Mechanistic studies indicated this transformation underwent a N‐alkylation‐hydroxylation‐transesterification cascade process. This research not only pushes the boundaries of the essential difunctionalization of alkenes but also exploits a new chemistry for azo compounds.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"79 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142782817","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Copper(I)-Mediated Site-Selective Tertiary δ–κ-C(sp3)–H Bond Chlorination of Ketones and Carboxylic Esters and Amides by Dichloramine-T 铜(I)-介导的δ -κ-C (sp3) -H键二氯胺对酮、羧酸酯和酰胺的氯化反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-04 DOI: 10.1002/adsc.202401324
Jordan Diaz, Yongsheng Zhang, James Merrett, Wai-Tsun Or, Philip Chan
{"title":"Copper(I)-Mediated Site-Selective Tertiary δ–κ-C(sp3)–H Bond Chlorination of Ketones and Carboxylic Esters and Amides by Dichloramine-T","authors":"Jordan Diaz, Yongsheng Zhang, James Merrett, Wai-Tsun Or, Philip Chan","doi":"10.1002/adsc.202401324","DOIUrl":"https://doi.org/10.1002/adsc.202401324","url":null,"abstract":"A synthetic method to prepare δ–κ-chloroketones, -esters and -amides that relies on the copper(I)-mediated chlorination at the unactivated tertiary δ–κ-C(sp&lt;sup&gt;3&lt;/sup&gt;)–H bond of ketones, and carboxylic esters and amides by dichloramine-T is presented. By exploiting the ability of the &lt;i&gt;N&lt;/i&gt;-chloramide to act as both the hydrogen atom transfer (HAT) and chlorination reagent, the reactions were shown to be site-selective with halogenation only occurring at the unactivated tertiary carbon center situated four to ten C–C bond distances away from the carbonyl functional group in the substrate. The site-selectivity of the chlorination protocol was further exemplified by the installing of the C–Cl bond at the distal position of one example containing two tertiary carbon centers and the late-stage functionalization of two drug molecules.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"12 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142776927","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Manganese Promoted Reductive Cross-Coupling of Phosphine Chlorides with Disulfides for the Synthesis of Thiophosphanes 锰促进氯代膦与二硫化物的还原交偶联合成硫代膦
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-04 DOI: 10.1002/adsc.202401395
Chao-Peng Zhang, Tian-Zhang Wang, Zhong-Jiang Yang, Yu-Feng Liang
{"title":"Manganese Promoted Reductive Cross-Coupling of Phosphine Chlorides with Disulfides for the Synthesis of Thiophosphanes","authors":"Chao-Peng Zhang, Tian-Zhang Wang, Zhong-Jiang Yang, Yu-Feng Liang","doi":"10.1002/adsc.202401395","DOIUrl":"https://doi.org/10.1002/adsc.202401395","url":null,"abstract":"Herein we reported a manganese promoted reductive cross-coupling approach to construct P‒S bond. This is a practical method for the synthesis of mono-thiophosphanes, bis-thiophosphanes and tri-thiophosphanes under mild conditions. The strategy featured a wide range of substrate scope including various disulfides and phosphine chlorides, constructing diverse sulfur-containing organophosphorus compounds from inodorous and readily available starting materials. The employment of reductive conditions avoided the generation of phosphorothioates (PV) by-products. Ultimately, gram-scale synthesis and applications were explored. Extensive experiments indicated that the phosphine radical cascade process was involved in the catalytic cycle.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"29 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142776926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Photocatalytic radical sulfonamidation/cyclization cascade towards sulfonaminated dihydrofurans and dihydroisoxazoles 磺化双氢呋喃和双氢异恶唑的光催化自由基磺化/环化级联反应
IF 5.4 2区 化学
Advanced Synthesis & Catalysis Pub Date : 2024-12-04 DOI: 10.1002/adsc.202401359
Zhichao Chen, Yuqiong Sheng, Qianwen Mou, Xiaolan Xie, Fengjiao Lv
{"title":"Photocatalytic radical sulfonamidation/cyclization cascade towards sulfonaminated dihydrofurans and dihydroisoxazoles","authors":"Zhichao Chen, Yuqiong Sheng, Qianwen Mou, Xiaolan Xie, Fengjiao Lv","doi":"10.1002/adsc.202401359","DOIUrl":"https://doi.org/10.1002/adsc.202401359","url":null,"abstract":"A general visible light induced photoredox-catalyzed radical sulfonamidation/cyclization cascade of olefinic carbonyls and β,γ-unsaturated oximes is described under mild and metal-free conditions. The protocol enables an efficient access to various sulfonaminated dihydrofurans and dihydroisoxazoles with moderate to good yields.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"19 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142776925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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