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Updated: May 5, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

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オルト対イプソ:アリルハリドを用いたサイト選択的なPdとノルボネン誘導アーレンのC-Hアミナーション

Zhe Dong1, Guangbin Dong

  • 1Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.

Journal of the American Chemical Society
|November 22, 2013
PubMed
まとめ

新しいパラジウム触媒反応により,C-H機能化を用いたオルトアレンアミネーションが可能になる. この方法は,アリルハリドを効率的に,高収量と機能群耐性を持つ有価なアミン製品に変換します.

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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