Dehalogenation of Aromatics by Nucleophilic Aromatic Substitution

Daniel Sadowsky; Kristopher McNeill; Christopher J. Cramer

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Dehalogenation of Aromatics by Nucleophilic Aromatic Substitution

机译：亲核性芳香取代对芳香族化合物的脱卤作用

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Nucleophilic aromatic substitution has been implicated as a mechanism for both the biotic and abiotic hydrodehalogenation of aromatics. Two mechanisms for the aqueous dehalogenation of aromatics involving nucleophilic aromatic substitution with hydride as a nucleophile are investigated using a validated density functional and continuum solvation protocol. For chlorinated and brominated aromatics, nucleophilic addition ortho to carbon-halogen bonds via an anionic intermediate is predicted to be the preferred mechanism in the majority of cases, while concerted substitution is predicted to be preferred for most fluorinated aromatics. Nucleophilic aromatic substitution reactions with the hydroxide and hydrosulfide anions as nucleophiles are also investigated and compared.

机译：亲核芳香族取代已被暗示为芳香族生物和非生物加氢脱卤的机制。使用经过验证的密度泛函和连续介质溶剂化方案，研究了涉及用氢化物作为亲核剂进行亲核芳族取代的芳族化合物的水脱卤机理。对于氯代和溴代芳族化合物，在大多数情况下，通过阴离子中间体向碳-卤素键邻位加亲核加成被认为是优选的机理，而对于大多数氟化芳族化合物，预计协同取代是优选的。还研究和比较了以氢氧根和氢硫化物阴离子为亲核试剂的亲核芳香族取代反应。

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《Environmental Science & Technology》 |2014年第18期|10904-10911|共8页
作者
Daniel Sadowsky; Kristopher McNeill; Christopher J. Cramer;
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作者单位

Institute of Biogeochemistry and Pollutant Dynamics, ETH Zurich, 8092 Zurich, Switzerland,Department of Chemistry, Chemical Theory Center, and Supercomputing Institute, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States;

Institute of Biogeochemistry and Pollutant Dynamics, ETH Zurich, 8092 Zurich, Switzerland;

Department of Chemistry, Chemical Theory Center, and Supercomputing Institute, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States;

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收录信息美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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1. Dehalogenation of Arenes via 5(N)2 Reactions at Bromine: Competition with Nucleophilic Aromatic Substitution. [J] . Gronert Scott, Garver John M., Nichols Charles M., The Journal of Organic Chemistry . 2014,第22期

机译：通过在溴的5（N）2反应进行的芳烃脱卤：与亲核芳香取代反应。
2. Synthesis of aromatic poly(ether ketone)s bearing 9,9-dialkylfluorene-2,7-diyl units through nucleophilic aromatic substitution polymerization [J] . Maeyama Katsuya, Ito Shin-nosuke Polymer bulletin . 2018,第12期

机译：通过亲核芳族取代聚合合成芳族聚（醚酮）轴承9,9-二烷基氟烯-2,7-二基单元
3. Intra- versus intermolecular electron transfer in radical nucleophilic aromatic substitution of dihalo(hetero)arenes – a tool for estimating π-conjugation in aromatic systems [J] . B. Janhsen, C. G. Daniliuc, A. Studer Chemical science . 2017,第5期

机译：在二卤代（杂）芳族芳族芳族取代中的分子间电子转移的血液分子 - 的分子间电子转移 - 用于估计芳族系统中π-缀合的工具
4. N-Heterocyclic Carbene-Catalyzed Nucleophilic Aromatic Substitution by α,β-Unsaturated Carbonyl Compounds via Umpolung [C] . Kosuke Yasui, Miharu Kamitani, Mamoru Tobisu 日本化学会春季年会講演予稿集 . 2018

机译：通过Umpolung通过α，β-不饱和羰基化合物催化N-杂环切菜催化的亲核芳香族取代
5. New tandem reactions involving nucleophilic aromatic substitution . [D] . Schammerhorn, James Ervin, III. 2011

机译：新的串联反应涉及亲核芳香取代。
6. Intra- versus intermolecular electron transfer in radical nucleophilic aromatic substitution of dihalo(hetero)arenes – a tool for estimating π-conjugation in aromatic systems [O] . B. Janhsen, C. G. Daniliuc, A. Studer 2017

机译：二卤代（杂）芳烃的自由基亲核芳族取代中的分子内和分子间电子转移–估算芳族体系中π共轭的工具
7. Studies on nucleophilic substitution reactions of aromatic compounds. II. A kinetic study on the nucleophilic substitution reactions of dinitrodiphenyl ethers or bromonitrobenzenes with sodium nitrophenoxides. [O] . Motonori TAKEDA, Isao KARATSUMA, Katsutoshi TAO, 1991

机译：芳族化合物的亲核取代反应研究。 II。二硝基苯醚与硝基氧化钠的二硝基苯醚或溴硝苯的亲核取代反应的动力学研究。

Dehalogenation of Aromatics by Nucleophilic Aromatic Substitution

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