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When transition-metal-catalyzed C–H activation meets allene chemistry 当过渡金属催化的C–H活化满足烯化学时
Tetrahedron chem Pub Date : 2023-09-22 DOI: 10.1016/j.tchem.2023.100049
Shu-Meng Deng, Yu-Xuan Zhao, Chengming Wang
{"title":"When transition-metal-catalyzed C–H activation meets allene chemistry","authors":"Shu-Meng Deng,&nbsp;Yu-Xuan Zhao,&nbsp;Chengming Wang","doi":"10.1016/j.tchem.2023.100049","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100049","url":null,"abstract":"<div><p>Transition-metal-catalyzed allenes-involved C–H functionalizations demonstrate unique selectivity and undergo exceptional pathways due to the existence of elusive orthogonal cumulative C<img>C<img>C bonds. As a result, it allows for a diverse array of C–H activation reactions, such as allylation, alkenylation, allenylation, dienylation, propargylation, and annulation. In this review, we comprehensively summarize the noteworthy aspects of transition-metal-catalyzed C–H functionalizations involving variously substituted allenes.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100049"},"PeriodicalIF":0.0,"publicationDate":"2023-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49710475","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
Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones 2-(4h-苯并[d][1,3]恶嗪-4-基)丙烯酸酯与2,4-二氢- 3h -吡唑-3-酮的有机催化区域和对映选择性(3+3)环化
Tetrahedron chem Pub Date : 2023-09-07 DOI: 10.1016/j.tchem.2023.100048
Zhongyue Lu, Xuling Chen, Pengfei Li
{"title":"Organocatalytic Regio- and Enantioselective (3+3)-Annulation of 2-(4H-Benzo[d][1,3]oxazin-4-yl)acrylates with 2,4-Dihydro-3H-pyrazol-3-ones","authors":"Zhongyue Lu,&nbsp;Xuling Chen,&nbsp;Pengfei Li","doi":"10.1016/j.tchem.2023.100048","DOIUrl":"10.1016/j.tchem.2023.100048","url":null,"abstract":"<div><p>A chiral sulfonamide-phosphine catalyzed regio- and enantioselective (3 + 3)-annulation of 2-(4<em>H</em>-benzo[<em>d</em>][1,3]oxazin-4-yl)acrylates with 2,4-dihydro-3<em>H</em>-pyrazol-3-ones has been established, affording a wide range of such 1,4,5,6-tetrahydropyrano [2,3-<em>c</em>]pyrazole-containing carboxylates in generally high yields (61–96%) with high diastereo- and enantioselectivities (8:1-&gt;20:1 dr, 85–95% ee). Based on several control experiments, a reaction mechanism was proposed. Importantly, the work represents the first example of using benzoxazinyl acrylates as three-atom synthons, which enriches the chemistry of benzoxazinyl acrylates.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100048"},"PeriodicalIF":0.0,"publicationDate":"2023-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49068883","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
The seriatim Cu(I) activation of 1,1,1′,1′-tetrapinacolborylethane to prospective ring closing 1,1,1 '，1 ' -四聚氨基甲酸乙酯的连续Cu(I)活化对预期闭合环的影响
Tetrahedron chem Pub Date : 2023-08-22 DOI: 10.1016/j.tchem.2023.100045
Sara González , Dario Del Carratore , Ricardo J. Maza , Elena Fernández
{"title":"The seriatim Cu(I) activation of 1,1,1′,1′-tetrapinacolborylethane to prospective ring closing","authors":"Sara González ,&nbsp;Dario Del Carratore ,&nbsp;Ricardo J. Maza ,&nbsp;Elena Fernández","doi":"10.1016/j.tchem.2023.100045","DOIUrl":"10.1016/j.tchem.2023.100045","url":null,"abstract":"<div><p>The synthesis and characterization of 1,1,1′1′-tetrapinacolborylethane is conducted to study the functionalization of that densely borylated small molecules through Cu-catalyzed coupling with allyl halides. A second Cu-catalyzed allylic alkylation of the homoallyl triboronate products gave access to mixed dihomoallyl diboronates. The intramolecular concatenated allylic alkylation version produced methylenecyclopentane-1,2-dipinacolboronic ester with 2:1 diastereoselection on the <em>trans</em>-diastereoisomer.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"8 ","pages":"Article 100045"},"PeriodicalIF":0.0,"publicationDate":"2023-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44117365","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 ring-closing reaction of enynols with aminals via methylene transfer and C–N bond activation 钯催化烯醇与胺盐通过亚甲基转移和C–N键活化的闭环反应
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100042
Bangkui Yu , Min Yu , Hanmin Huang
{"title":"Palladium-catalyzed ring-closing reaction of enynols with aminals via methylene transfer and C–N bond activation","authors":"Bangkui Yu ,&nbsp;Min Yu ,&nbsp;Hanmin Huang","doi":"10.1016/j.tchem.2023.100042","DOIUrl":"10.1016/j.tchem.2023.100042","url":null,"abstract":"<div><p>The aminomethyl cyclopalladated complex is identified as a key intermediate for promoting the C–N bond activation of tertiary amines via reductive elimination and oxidative addition sequence. This strategy has enabled a palladium-catalyzed ring-closing reaction of enynols with aminals via methylene transfer and C–N bond activation, which provides rapid access to densely functionalized <em>O</em>-heterocycle containing allenic amines. The dual roles of the cyclopalladated complex, first as an aminomethylene-carrying reagent and then as a catalyst for C–N bond activation, have enabled a rare cascade redox-neutral methylene transfer and cyclization process that can simultaneously construct <em>O</em>-heterocycle framework and allenic amine functionality.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100042"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48905725","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
Organocatalytic activation of cyclopropanes in asymmetric synthesis 不对称合成环丙烷的有机催化活化
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100041
Efraím Reyes, Uxue Uria, Liher Prieto, Luisa Carrillo, Jose L. Vicario
{"title":"Organocatalytic activation of cyclopropanes in asymmetric synthesis","authors":"Efraím Reyes,&nbsp;Uxue Uria,&nbsp;Liher Prieto,&nbsp;Luisa Carrillo,&nbsp;Jose L. Vicario","doi":"10.1016/j.tchem.2023.100041","DOIUrl":"10.1016/j.tchem.2023.100041","url":null,"abstract":"<div><p>Cyclopropanes are strained carbocycles that can undergo ring opening reactions in which one of the C–C bond present in the cycle is broken following a radical or ionic mechanism. Recently, organocatalysis has emerged as a convenient tool for promoting these ring-opening processes under very mild reaction conditions and allowing the unconventional preparation of interesting compounds starting from differently substituted cyclopropanes. In this review, we present the different reactions developed in this field in which different organocatalytic activation manifolds have been employed to trigger the ring opening event.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100041"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46385649","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 (II)-catalyzed cascade reactions initiated with directed activation of unactivated sp3 C–H bonds 钯(II)催化的级联反应由未激活的sp3 C-H键的定向激活引发
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100046
Robbie Ge , Faith Herington , Alana Mangawang , Debabrata Maiti , Haibo Ge
{"title":"Palladium (II)-catalyzed cascade reactions initiated with directed activation of unactivated sp3 C–H bonds","authors":"Robbie Ge ,&nbsp;Faith Herington ,&nbsp;Alana Mangawang ,&nbsp;Debabrata Maiti ,&nbsp;Haibo Ge","doi":"10.1016/j.tchem.2023.100046","DOIUrl":"10.1016/j.tchem.2023.100046","url":null,"abstract":"<div><p>Cascade reactions—chemical processes consisting of two or more reactions in one pot—offer considerable advantages in terms of time, cost, atom efficiency, and reduced waste generation, and have thus unsurprisingly attracted considerable attention amongst the chemical community in recent decades. On the other hand, transition metal-catalyzed site-selective carbon-hydrogen (C–H) bond functionalization represents one of the most significant and efficient synthetic approaches in organic chemistry, enabling the conversion of common petroleum chemicals into highly valuable products in a single step. Utilization of this approach in cascades dramatically improves its applicability by allowing for the efficient construction of complex molecules from simple starting materials in a single pot. This perspective summarizes the developments in palladium (II)-catalyzed cascade reactions initiated with directed activation of unactivated aliphatic C–H bonds and our recent efforts in synthesizing bicyclic lactones, followed by current challenges and future opportunities.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100046"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46643525","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
Photoredox-enabled remote radical group migration: Pathway to 1,7-dicarbonyl compounds from diazoalkanes 光氧化还原激活的远程自由基迁移:从重氮烷烃到1,7-二羰基化合物的途径
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100040
Hai-Bing Ye , Ye-Peng Bao , Tian-Yang Liu , Tao Wei , Chen Yang , Qing-An Liu , Jun Xuan
{"title":"Photoredox-enabled remote radical group migration: Pathway to 1,7-dicarbonyl compounds from diazoalkanes","authors":"Hai-Bing Ye ,&nbsp;Ye-Peng Bao ,&nbsp;Tian-Yang Liu ,&nbsp;Tao Wei ,&nbsp;Chen Yang ,&nbsp;Qing-An Liu ,&nbsp;Jun Xuan","doi":"10.1016/j.tchem.2023.100040","DOIUrl":"10.1016/j.tchem.2023.100040","url":null,"abstract":"<div><p>Herein, we developed a mild and efficient photoredox-enabled remote radical group migration with the utilization of diazoalkanes as radical precursors, giving access to various valuable 1,7-dicarbonlys in moderate to good yields. A diverse set of migrating groups, including benzothiazole, benzothiophene, pyrazine, pyridine, thiazole, thiophene and nitrile were well tolerated. Furthermore, the facile synthesis of 1,8-dicarbonyl compound, scale-up reaction and useful synthetic transformation further proved the method attractive and valuable.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100040"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42845939","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
NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation NHC催化Ynones与三氟甲基酮的区域收敛转化：Aldol反应或[3+2]环化
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100044
Fangfang Lu , Bai Shi , Wei Cao, Huiping Yin, Tianjiao Huang, Kai Zhang, Changsheng Yao
{"title":"NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation","authors":"Fangfang Lu ,&nbsp;Bai Shi ,&nbsp;Wei Cao,&nbsp;Huiping Yin,&nbsp;Tianjiao Huang,&nbsp;Kai Zhang,&nbsp;Changsheng Yao","doi":"10.1016/j.tchem.2023.100044","DOIUrl":"10.1016/j.tchem.2023.100044","url":null,"abstract":"<div><p>A novel NHC-catalyzed regiodivergent reaction of ynones with trifluoromethyl ketones consisting of Aldol reactions and intermolecular [3 + 2] annulations has been developed. Employing two different NHC catalysts, various tertiary alcohols and dihyrofuranones containing trifluoromethyl can be obtained in moderate to good yields (35 examples, up to 91% yield). This protocol features mild reaction conditions, high efficiency and broad substrates scope, promoting the development of NHC catalysis and transformations of ynones.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100044"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47720545","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
Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols 手性反阴离子控制的金催化氢胺化/ β-氨基-1,4-烯醇对映选择性1,3-烯丙醇异构化的化学选择性
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100043
Lorenzo Carli, Anyawan Tapdara, Jianwen Jin, Yichao Zhao, Philip Wai Hong Chan
{"title":"Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols","authors":"Lorenzo Carli,&nbsp;Anyawan Tapdara,&nbsp;Jianwen Jin,&nbsp;Yichao Zhao,&nbsp;Philip Wai Hong Chan","doi":"10.1016/j.tchem.2023.100043","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100043","url":null,"abstract":"<div><p>A synthetic method for the preparation of 1,8-dihydroindeno[2,1-<em>b</em>]pyrroles and pyrrol-2-yl methanols in an enantioselective manner that relies on the chiral gold(I)-catalysed reactions of <em>β</em>-amino-1,4-enynols is described. A divergence in product selectivity was achieved by exploiting the electrostatic interactions between the chiral counteranion of the metal catalyst and the substrate. With a gold(I) complex containing a chiral <em>N</em>-triflyl phosphoramide-based counteranion, tandem dehydrative Nazarov-type electrocyclisation/hydroamination of the substrate was found to selectively occur to afford the indeno-fused pyrrole adduct. In contrast, changing to a chiral phosphate-based counteranion was observed to result in a hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation cascade pathway to give the 1<em>H</em>-pyrrole derivative.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100043"},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49710023","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
Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols 手性反阴离子控制的金催化氢胺化/ β-氨基-1,4-烯醇对映选择性1,3-烯丙醇异构化的化学选择性
Tetrahedron chem Pub Date : 2023-08-01 DOI: 10.1016/j.tchem.2023.100043
L. Carli, Anyawan Tapdara, Jianwen Jin, Yichao Zhao, P. Chan
{"title":"Chiral counteranion controlled chemoselectivity in gold catalysed hydroamination/enantioselective formal 1,3-allylic alcohol isomerisation of β-amino-1,4-enynols","authors":"L. Carli, Anyawan Tapdara, Jianwen Jin, Yichao Zhao, P. Chan","doi":"10.1016/j.tchem.2023.100043","DOIUrl":"https://doi.org/10.1016/j.tchem.2023.100043","url":null,"abstract":"","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"55175405","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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