芳基重氮盐的偶联反应.pdf

有机化学有机化学 Chinese Journal of Organic Chemistry REVIEW * E-mail: Received April 2, 2014; revised April 24, 2014; published online May 7, 2014. Project supported by the National Natural Science Foundation of China (No. 21402123), the Zhejiang Provincial Natural Science Foundation of China (No. LQ14B020001), the Science Technology Department of Zhejiang Province (No. 2012R10014-15), the Education Department of Zhejiang Province (No. Y201328443) and the Science Technology Project of Shaoxing City (No. 2013014017). 国家自然科学基金(No. 21402123)、浙江省自然科学基金(No. LQ14B020001)、浙江省科技厅(No. 2012R10014-15)、浙江省教育厅(No. Y201328443) 和绍兴市科技计划(No. 2013014017)资助项目. Chin. J. Org. Chem. 2014, 34, 17431758 2014 Chinese Chemical Society 偶联反应; 碳碳键的构筑; 绿色合成 Research Progress on Cross-Coupling with Aryl Diazonium Salts Xuan, Shangci Wang, Xiaodan Wang, Jianwei Zhao, Baoli Cheng, Kai* Qi, Chenze (Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000) Abstract Aryl diazonium salts have been widely used in cross-coupling reaction due to its easily available and highly reac- tivity as arylation reagents, which have drawn more and more attention by chemists in organic synthesis in recent years. The research progress since 2006 on cross-coupling with aryl diazonium salts combined with our work is reviewed, focusing on new applications and new progress of aryl diazonium salts in new method to build carbon-carbon bond, with construction of the natural product skeleton, in the field of heterogeneous catalysis and other aspects of green synthesis. Keywords aryl diazonium salts; cross-coupling; construction of CC bond; green synthesis 在钯催化的偶联反应中, 卤代烃是一类最常见的亲 电试剂, 该类型反应能否顺利进行的关键环节是过渡金 属插入碳卤键从而来启动催化循环. 溴代烃、碘代烃虽 然反应活性相对较高但是制备成本高, 而较便宜且易得 的氯代烃反应活性很低, 难以发生金属插入启动反应, 而且卤代烃在反应进行的过程中生成大量废物卤化物 盐, 易对环境造成较大的危害. 而用磺酸苯酯类的亲电 试剂来代替卤代烃, 也仍然存在着一些不足, 如 CO 键难以断裂而导致的反应活性较低, 使得反应往往需要 较高温度, 由于大体积的离去基团增加后处理的难度 等, 限制了其进一步的应用. 近年来, 经由 CN 键活 化而不是 CX 键或 CO 键断裂启动金属催化循环来 构筑化合物的方法已经成为有机金属化学研究的新途 径和新思路. 在这类研究中, 芳基重氮盐因其独特的性 质成为偶联反应中极具研究价值的亲电试剂, 成为新的 研究热点. 其主要原因在于芳基重氮盐具有以下特点: (1)芳基重氮盐可以很容易地由廉价的芳香胺合成, 而且收率很高, 几乎可以定量得到, 易于大量制备且便 于操作. (2)在钯催化的偶联反应中, 芳基重氮盐作为亲电 试剂的反应活性高于其对应的卤代烃和芳香酯. 在反应 中随着氮气分子的离去形成芳香钯中间体来启动催化 循环, 该步骤通过热力学计算可知其所需要能量很低, 室温下就能进行, 一般不会成为反应的决速步. (3)以重氮盐为亲电试剂的偶联反应条件都较温和, 一般在室温下就能进行, 且通常不需要加入碱或配体等 作为添加剂, 易于后处理和分离. (4)重氮基团在反应中以氮气分子的形式离去, 无 有机化学 综述与进展 1744 http:/sioc- 2014 Chinese Chemical Society 而用叔丁醇作溶剂则是以三组分反应为主(Eq. 19). 作 者基于此提出的机理也是以 Heck 反应途径先发生, 钯 重新插入的中间体被苯硼酸捕捉形成三组分反应. MeO N2BF4 B(OH)2 MeO OMe OMe + + + 5 mol% Pd2(dba)3 CHCl3 1.2 equiv. base solvent (0.05 mol/L) r.t., 12 h 1 equiv. 55 kPa 1.2 equiv. (19) + . Antunes 等23报道了芳基重氮盐在有氧的条件下, Pd 催化下发生 Baylis-Hillman 加合反应得到 -苄基- 酮酯. 该合成方法类似于芳基重氮盐参与的 Heck 反应, 但由于底物加成后的含钯中间体的 -消除方向不同而 生成了不同的产物(Eq. 20). Correia 等24报道了一种钯催化的吲哚、 苯并呋喃和 苯并噻吩的 CH 芳基化反应. 有意思的是, 吲哚、苯 并呋喃芳基化的位置是 C-2 位, 而苯并噻吩则发生在 C-3 位上. 这可能是由于形成的芳钯正离子中间体的稳 定性所决定的(Scheme 3). R1OCH3 OHO N2BF4 R1OCH3 OO Pd(OAc)2 (1 2 mol%) EtOH, 70 oC R1 = CH2CH3; R1 = p-NO2C6H4 or R1 = Hexyl (20) N Me N2BF4 R N Me R Pd(OAc)2 O N2BF4 R R Pd(OAc)2 O S N2BF4 R Pd(OAc)2 S R + H2O/IPE (2:1) (open flask) + MeOH (open flask) + MeOH (open flask) Scheme 3 2 天然产物骨架的构建天然产物骨架的构建 芳基重氮盐参与的 Heck 反应由于其良好的化学选 择性和极温和的反应条件使得其在天然产物的合成中 扮演了重要角色. Correia 课题组多年以来一直致力于芳 基重氮盐参与的 Heck-Matsuda 反应在天然产物合成方 面的应用. 早在 2003 年, Correia25就发展了一种室温下 环状烯胺通过芳基化短时间内即可构筑(2S,5R)-苯基脯 氨酸甲酯结构, 可以来合成 Schramms C-Azanucleoside (Eq. 21). N R1 OMe CO2R2 AcONa N R1 CO2R2 OMe N2BF4 OH HO OH N H H2N Schramms C-azanucleoside Pd2(dba)3 dba MeCN, r.t. (21) . + Correia 等26报道了顺丁烯二酸酐的单或者双芳基 化来合成海洋类生物碱 Prepolycitrin A 和 Polycitrin A (Scheme 4). Correia 等27报道了立体选择性的手性二氢呋喃的 Heck-Matsuda 型芳基化, 并以此为关键步骤完成了()- 有机化学 综述与进展 1748 http:/sioc- 2014 Chinese Chemical Society 但在加入 TBAF 起相转移促进作用 就可以顺利发生; 当芳基氟硼酸盐同芳基重氮盐发生 Suzuki 反应时, 必须加入碱才能获得较高转化率 (Scheme 27). N2BF4 ArSi(OR)3 TBAF Hiyama Suzuki-Miyaura ArBF3K in water base + - ArArArAr Ar Scheme 27 我们75在此基础上又发展了一种钯催化的芳香胺 Chinese Journal of Organic Chemistry REVIEW Chin. J. Org. Chem. 2014, 34, 17431758 2014 Chinese Chemical Society Fouquet, E.; Felpin, F. X. Adv. Synth. Catal. 2011, 353, 3063. 2 Li, Y. W.; Yan, X. Y.; Li, X.; Chang, H.-H.; Wei, W. L. Shanxi Chem. Ind. 2011, 31, 33. 3 Taylor, J. G.; Moro, A. V.; Correia, C. R. D. Eur. J. Org. Chem. 2011, 1403. 4 Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236. 5 Mo, F.; Dong, G.; Zhang, Y.; Wang, J. Org. Biomol. 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