酞菁铁催化烯烃自由基膦叠氮化反应: 利用叠氮快速转移合成膦叠氮的温和方法

doi:10.1016/S1872-2067(21)63847-0

催化学报 ›› 2021, Vol. 42 ›› Issue (10): 1634-1640.DOI: 10.1016/S1872-2067(21)63847-0

酞菁铁催化烯烃自由基膦叠氮化反应: 利用叠氮快速转移合成膦叠氮的温和方法

马晓旭^a^,^b, 邱盟峯^a, 葛亮^a, 李晓岩^a, 李亚军^a, 吴莉^b, 鲍红丽^a^,^c()

^a中国科学院福建物质结构研究所, 分子合成卓越中心, 结构化学重点实验室, 煤制乙二醇及相关技术重点实验室, 福建福州350002
^b武汉工程大学化学与环境工程学院, 湖北武汉430205
^c中国科学院大学, 北京100049

收稿日期:2021-05-21 接受日期:2021-05-22 出版日期:2021-06-20 发布日期:2021-06-20
通讯作者: 鲍红丽
作者简介:*电话: (0591)63179307; 电子信箱:hlbao@fjirsm.ac.cn
基金资助:
国家重点基础研究发展计划(2017YFA0700103);国家自然科学基金(21922112);国家自然科学基金(21871258);国家自然科学基金(22001251);中国科学院战略性重点研究计划(XDB20000000)

Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: A facile synthesis of β-azido-phosphine oxide with a fast azido transfer step

Xiaoxu Ma^a^,^b, Mong-Feng Chiou^a, Liang Ge^a, Xiaoyan Li^a, Yajun Li^a, Li Wu^b, Hongli Bao^a^,^c()

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, Fujian, China
^bSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, Hubei, China
^cUniversity of Chinese Academy of Sciences, Beijing 100049, China

Received:2021-05-21 Accepted:2021-05-22 Online:2021-06-20 Published:2021-06-20
Contact: Hongli Bao
Supported by:
National Key R&D Program of China(2017YFA0700103);National Natural Science Foundation of China(21922112);National Natural Science Foundation of China(21871258);National Natural Science Foundation of China(22001251);Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)

摘要/Abstract

摘要：

含氮和磷原子的化合物是生命系统中不可缺少的组成部分, 由于其独特的化学、生物和物理性质, 已被广泛应用于农业化学、材料科学和制药学. 如果一个有机化合物同时含有氮和磷原子, 它可能因为胺和膦/磷酸盐基团的协同作用而具有额外的功能. 2015年赵玉芬院士和唐果教授报道了一例自由基叠氮膦酰化的例子, 该反应虽然有效, 但因需使用化学剂量的氧化性自由基引发剂Mn(OAc)₃·2H₂O, 因此, 有必要发展一种更环保经济的方法.
本文报道了铁催化烯烃的分子间自由基膦叠氮化反应. 该方法使用了微量的催化剂, 通过自由基接力与叠氮基团转移实现分子间自由基膦叠氮化反应. 实验先进行条件筛选, 考察了催化剂类型、催化剂用量、氧化剂类型、溶剂和温度对反应的影响, 确定以酞菁铁为催化剂, 叔丁基过氧化氢(TBHP)为引发剂, 乙腈为溶剂, 苯乙烯、叠氮基三甲基硅烷、二苯基膦酰为模板反应底物为最佳条件, 实现了二苯基膦酰对烯烃的自由基膦酰基叠氮化反应. 在最优条件下进行底物拓展, 制备得到27种膦叠氮化合物, 产率为23%~88%. 以制得的膦叠氮产物为起始原料, 通过叠氮还原和Click反应制备得到三种衍生物, 产率为82%~97%, 可作为药物合成中间体进行下一步研究.
本文还进行了机理实验和理论计算. 在自由基钟实验和自由基捕获实验中, 通过两种不同速率的自由基开环反应与自由基捕获反应证实了反应的自由基路径. 质谱检测到酞菁铁羟基(PcFe^IIIOH)和酞菁铁叠氮(PcFe^IIIN₃)的存在. 采用密度泛函理论计算了不同自旋态下的酞菁铁(PcFe), 以确定可能的催化剂种类, 并计算出三重态³PcFe最稳定. 从三重态³PcFe开始计算铁催化叔丁基过氧化氢的单电子转移, 并计算了从叔丁氧基自由基开始的自由基接力, 证实了膦酰苄基自由基的形成是最有利的途径; 研究结果发现膦酰苄基自由基能与⁴PcFe(N₃)反应, 发生叠氮基团转移生成目标产物. 在叠氮基团转移计算中, 考察了四种合理的途径, 分别是苄基在三重态或五重态势能面接近叠氮基团的内部或端位氮原子(N_i和N_t). 结果表明, 叠氮基团从叠氮基酞菁铁(III)物种(PcFe^IIIN₃)转移到苄基自由基的活化能(4.8 kcal/mol)极低. 据此催化循环机理可能为: 酞菁铁首先与叔丁基过氧化氢发生单电子转移形成酞菁铁羟基中间体及叔丁氧自由基; 然后, 二苯基膦酰的氢原子被叔丁氧自由基攫取生成二苯基膦酰自由基, 并加成至苯乙烯形成苄基自由基. 同时, 酞菁铁羟基中间体与HN₃进行配体交换形成酞菁铁叠氮中间体, 最后与苄基自由基进行叠氮基团转移生成产物, 并重新生成酞菁铁(II).
本文证实了铁催化叠氮化反应的自由基基团转移机理(外球机理), 因为很难想象如何在酞菁铁的同侧同时加成叠氮与苄基基团, 通过生成高价铁物种(PcFe-N₃·)的内球机理得到产物. 该工作将有助于启发更多的金属催化机理研究.

关键词: 酞菁铁, 磷酰基叠氮化, 双官能团化, 自由基基团转移, 密度泛函理论计算

Abstract:

Phosphinoylazidation of alkenes is a direct method to build nitrogen- and phosphorus-containing compounds from feed-stock chemicals. Notwithstanding the advances in other phosphinyl radical related difunctionalization of alkenes, catalytic phosphinoylazidation of alkenes has not yet been reported. Here, we describe the first iron-catalyzed intermolecular phosphinoylazidation of styrenes and unactivated alkenes. The method is practically useful and requires a relatively low loading of catalyst. Mechanistic studies confirmed the radical nature of the reaction and disclosed the unusually low activation energy 4.8 kcal/mol of radical azido group transfer from the azidyl iron(III) phthalocyanine species (PcFeIIIN3) to a benzylic radical. This work may help to clarify the mechanism of iron-catalyzed azidation, inspire other mechanism studies and spur further synthetic applications.

Key words: Iron phthalocyanine, Phosphinoylazidation, Difunctionalization, Radical group transfer, Density functional theory calculation

马晓旭, 邱盟峯, 葛亮, 李晓岩, 李亚军, 吴莉, 鲍红丽. 酞菁铁催化烯烃自由基膦叠氮化反应: 利用叠氮快速转移合成膦叠氮的温和方法[J]. 催化学报, 2021, 42(10): 1634-1640.

Xiaoxu Ma, Mong-Feng Chiou, Liang Ge, Xiaoyan Li, Yajun Li, Li Wu, Hongli Bao. Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: A facile synthesis of β-azido-phosphine oxide with a fast azido transfer step[J]. Chinese Journal of Catalysis, 2021, 42(10): 1634-1640.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(21)63847-0

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图/表 10

Fig. 1. Biologically important nitrogen-containing phosphonates and the phosphinoylazidation of alkenes.

Fig. 2. Metal-involved radical azido group transfer.

Table 1 Optimization of the reaction conditions. a

Entry	Variation from “standard conditions”	Yield (%)^b
1	Standard reaction conditions ^a	84
2 ^c	Fe(OTf)₂ instead of PcFe	27 ^d
3 ^c	AgNO₃ instead of PcFe	trace ^d
4^c	AgOTf instead of PcFe	trace ^d
5^c	Mn(OAc)₂·4H₂O instead of PcFe	trace ^d
6	40 ^oC instead of rt	43
7	70 ^oC instead of rt	11
8	THF instead of CH₃CN	17
9	PhCl instead of CH₃CN	56
10	1,4-Dioxane instead of CH₃CN	49
11	LPO instead of TBHP	78
12	NFSI instead of TBHP	0
13 ^e	5 mmol reaction	87

Fig. 3. Substrate scope of alkenes. a,b

Fig. 4. Substrate scope of phosphorous substrates. a,b

Fig. 5. Further transformations of products.

Fig. 6. Radical clock and radical trapping experiments.

Fig. 7. The free energy profile for the formation of iron-azide species from 3PcFe.

Fig. 8. Transition states of azide transfer refer to through internal and terminal nitrogen, Ni and Nt, on triplet and quintet surfaces. Spin density isosurfaces of 3TS3-Ni and 5TS3-Nt are displayed.

Fig. 9. Proposed PcFe-catalyzed phosphinoylazidation mechanism.

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酞菁铁催化烯烃自由基膦叠氮化反应: 利用叠氮快速转移合成膦叠氮的温和方法

Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: A facile synthesis of β-azido-phosphine oxide with a fast azido transfer step

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