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RSC主编推荐:有机领域精彩文章快览(免费阅读原文)

英国皇家化学会(RSC)是一个拥有175年历史的面向全球化学家的非营利会员制机构,旗下拥有43种期刊,其中很多在化学领域有很高影响力。为了进一步帮助广大读者追踪科技前沿热点,X-MOL团队与英国皇家化学会合作,推出英国皇家化学会期刊主编推荐的精彩文章快览,本期文章属“有机领域”,英文点评来自英国皇家化学会期刊的主编。如果大家对我们的解读有更多的补充和点评,欢迎在文末写评论发表您的高见!


Organic Chemistry Frontiers (IF: 4.955)



1. Efficient trifluoromethylation via the cyclopropanation of allenes and subsequent C–C bond cleavage  

Org. Chem. Front., 2017, Advance Article

DOI: 10.1039/C7QO00419B



CF3-substituted vinylic cyclopropanes was highly selectively formed by a copper-catalyzed cyclic trifluoromethylation of (4,4-disubstituted-2,3-butadienyl) malonates with Togni's reagent II, in which the trifluoromethyl group was installed at the middle carbon of the allene unit by applying 1,10-phenanthroline as the ligand. Such unique cyclopropanes successfully bring the trifluoromethyl group to other useful organic skeletons by the selective cleavage of C–C bonds with an exclusive diastereoselectivity. Based on the mechanistic studies, an allene radical addition, oxidation, and allylic substitution pathway has been proposed.


本文作者以铜催化的(4,4-二取代-2,3-丁二烯基)丙二酸酯与Togni试剂II的环化三氟甲基化反应,高选择性地生成了CF3取代的乙烯基环丙烷,反应以1,10-菲咯啉作为配体,三氟甲基基团位于联烯的中间碳位。这种独特的环丙烷结构可以通过高度非对映选择性的C-C键的断裂将三氟甲基基团成功引入其他有用的有机骨架上。机理研究表明反应经历联烯的自由基加成、氧化和烯丙基取代的途径。


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2. Silver-mediated fluorination of alkyl iodides with TMSCF3 as the fluorinating agent

Org. Chem. Front., 2017, Advance Article

DOI: 10.1039/C7QO00450H



The first example of a silver-mediated fluorination of alkyl iodides with the Ruppert–Prakash reagent (TMSCF3) as a fluorinating agent has been reported. This reaction is compatible with a variety of functional groups and proceeds under mild reaction conditions. Moreover, we demonstrate that the large surface area of CaF2 dramatically increased the reaction yield.


本文报道了第一例使用Ruppert-Prakash 试剂(TMSCF3)作为氟化试剂参与银介导的烷基碘氟化反应。该反应可在温和的条件下进行,对多种官能团兼容。此外,研究人员还证明CaF2的高表面积显著提高了反应产率。


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Chemical Science (IF: 8.668)



1. Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization

Chem. Sci., 2017, 8, 5299-5304

DOI: 10.1039/C7SC01732D



Researchers in Singapore have demonstrated that pivalophenone N-H imine serves as an excellent substrate for cobalt-catalyzed C-H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively. The increased steric bulk in the ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion. This two-step protocol could be attractive for the preparation of ortho-alkylated aryl nitriles via C-H activation.


新加坡南洋理工大学研究人员报道了以叔丁基苯基亚胺为底物分别与溴代烷烃及氯代芳香烃发生Co催化的C-H键烷基化或芳基化反应。邻位取代的叔丁基苯基亚胺可通过提高的空间位阻效应高效地转化为腈。这种非常具有吸引力的两步法有望用于通过C-H键活化制备邻位烷基化芳香腈。


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2. Identifying the first folded alkylbenzene via ultraviolet, infrared, and Raman spectroscopy of pentylbenzene through decylbenzene

Chem. Sci., 2017, 8, 5305-5318

DOI: 10.1039/C7SC02027A


Scientists in the USA and Germany have identified the first folded alkylbenzene by studying conformational preferences for pentyl- to decybenzene. Using a combination of ultraviolet, infrared and Raman spectroscopic methods, researchers identified and characterized folded chain structures in which the chain comes back over the phenyl π cloud. Future work will focus on characterising structures with increasing alkyl chain lengths.


通过研究戊基苯到癸基苯的构象偏好,美国和德国的科学家首次确认了折叠构象的烷基苯。利用紫外、红外和拉曼光谱等方法,他们确定并表征了折叠的链结构,其中链折回到苯的π电子云之上。未来的研究工作将进一步着重于更长烷基链的结构表征。


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