氧气氧化铜催化的苯胺邻位叠氮化反应

doi:10.6023/A19020070

摘要/Abstract

叠氮取代的苯胺是有机合成中应用广泛的结构单元. 通过C—H键活化策略来制备叠氮基苯胺衍生物往往需要使用当量的剧烈氧化剂, 造成反应的整体原子经济性低, 官能团耐受性差. 本文使用廉价、绿色的氧气作为最终氧化剂, 发展了高效的铜催化苯胺C—H键叠氮化的方法. 该转化具有反应条件温和、区域选择性单一和官能团兼容性广等优点.

关键词: 氧气, 苯胺, 叠氮化, 碳-氢键活化, 铜催化

Organic azides are widely used in chemical synthesis, drug discovery, bioconjugation, and material science, owing to their flexible transformations to useful chemicals such as amines, amides, isocyanates and heterocycles. In light of the diverse value of azide-containing compounds, numerous synthetic methods have been established to access this significant functionality. Among them, direct C—H azidation reactions have attracted particular attention due to their cost- and atom-efficiency. Previous methods for the preparation of azido-substituted anilines require the employment of stoichiometric amount of harsh oxidants such as hyperoxides and hypervalent iodine reagents. To synthesize these valuable compounds in an economical and environmentally benign manner, a simple and efficient copper-catalyzed ortho C—H azidation of anilines using molecular oxygen as terminal oxidant has been developed. The reaction proceeded smoothly with the assistance of pyridine at room temperature, and afforded the synthetically useful azido-substituted anilines in moderate to good yields. Notably, the process of dehydrogenation coupling of anilines to azo compounds was significantly suppressed in this protocol. This method allows for the highly regioselective formation of C—N₃ bonds under mild reaction conditions, and exhibits good functional group and substrate scope compatibility. A general procedure for the azidation of anilines is as follows: a mixture of aniline (0.4 mmol) and CuBr (5.7 mg, 0.04 mmol) is loaded in a 20 mL Schlenk tube, which is equipped with a magnetic stir bar and subjected to evacuation/flushing with oxygen three times. Subsequently, DCM (4.0 mL), pyridine (6.3 mg, 0.08 mmol) and TMSN₃ (92.2 mg, 0.8 mmol) are added to the Schlenk tube via syringe, and the formed mixture is stirred at room temperature until the amount of target product no longer increases, which is monitored by TLC. After completion of the reaction, the solution is concentrated under vacuum and further purified by column chromatography on silica gel to give the desired product (eluent: petroleum ether/ethyl acetate).

Key words: molecular oxygen, aniline, azidation, C—H bond activation;, copper catalysis

引用此文

林凤闺蓉, 梁宇杰, 郦鑫耀, 宋颂, 焦宁. 氧气氧化铜催化的苯胺邻位叠氮化反应[J]. 化学学报, 2019, 77(9): 906-910.

Lin, Fengguirong, Liang, Yujie, Li, Xinyao, Song, Song, Jiao, Ning. Copper-catalyzed ortho C-H Azidation of Anilines Using Molecular Oxygen as Terminal Oxidant[J]. Acta Chimica Sinica, 2019, 77(9): 906-910.

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图/表 6

图式1. 苯胺衍生物的直接C—H键叠氮化反应

Scheme 1. Direct C—H azidation of aniline derivatives

表1. 反应条件优化a

Table 1. Optimization of reaction conditions a

表2. 苯胺的底物范围a

Table 2. Optimization of reaction conditions a

表3. 邻位不含取代基的苯胺的叠氮化反应a,b

Table 3. Azidation of non-ortho-substituted anilines a,b

图式2. 反应产物的转化

Scheme 2. Transformation of 2a

图式3. 推测的反应机理

Scheme 3. Proposed mechanism

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