氮杂环磷氢试剂的氢转移活性研究进展

doi:10.6023/cjoc202304023

有机化学 ›› 2023, Vol. 43 ›› Issue (11): 3806-3825.DOI: 10.6023/cjoc202304023 上一篇下一篇

综述与进展

氮杂环磷氢试剂的氢转移活性研究进展

张雨杉^a†, 桓臻^a†, 杨金东^a^,^*(), 程津培^a^,^b^,^c

a 清华大学化学系基础分子科学中心北京 100084
b 南开大学化学学院元素有机化学国家重点实验室天津 300071
c 物质绿色创造与制造海河实验室天津 300192

收稿日期:2023-04-19 修回日期:2023-05-22 发布日期:2023-06-26
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(22222106); 国家自然科学基金(21973052); 国家自然科学基金(22193011); 国家自然科学基金(21933008); 物质绿色创造与制造海河实验室资助项目.

Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines

Yushan Zhang^a†, Zhen Huan^a†, Jindong Yang^a(), Jinpei Cheng^a^,^b^,^c

a Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084
b State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
c Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192

Received:2023-04-19 Revised:2023-05-22 Published:2023-06-26
Contact: * E-mail: jdyang@mail.tsinghua.edu.cn
About author:
^†These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22222106); National Natural Science Foundation of China(21973052); National Natural Science Foundation of China(22193011); National Natural Science Foundation of China(21933008); Haihe Laboratory of Sustainable Chemical Transformations

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摘要/Abstract

氮杂环磷氢(NHP-H)独特的杂环骨架赋予了其优异的负氢还原能力. 过去十年间, NHP-H被广泛用于极性不饱和底物的负氢还原中. 近年来, 随着自由基化学的兴起, 其在催化自由基还原领域崭露头角, 方兴未艾. 这种新的NHP-H反应模式有望突破负氢机理对底物极性的限制, 可大大拓展底物的适用范围. 简要总结了NHP-H在负氢还原和自由基还原中的合成应用, 重点关注其自由基反应相关的性质, 包括NHP自由基及其前体的结构、性质、合成应用等.

关键词: 氮杂环磷氢, 有机催化, 自由基活性, 负氢还原, 构效关系

The unique heterocyclic skeletons of N-heterocyclic phosphines (NHP-H) endow them with excellent hydridic reactivity, which have enabled a great array of catalytic hydrogenations of unsaturated substrates in the past decade. Recently, applications of NHP-H in radical reductions, especially in a catalytic fashion, have emerged as a promising forefront area. This new reaction pattern, distinctive from but complementary to the well-established hydride pathway, can greatly expand the reaction scope to σ-bond scission. Herein, some representative examples of synthetic applications of NHP-H in both hydridic and radical reductions with emphasis on their radical reactivity are briefly summarized, including the structural and property studies of NHP radicals and their precursors as well as their applications in radical hydrogenations.

Key words: N-heterocyclic phosphine, organocatalysis, radical reactivity, hydridic reduction, structure-reactivity relationship

引用此文

张雨杉, 桓臻, 杨金东, 程津培. 氮杂环磷氢试剂的氢转移活性研究进展[J]. 有机化学, 2023, 43(11): 3806-3825.

Yushan Zhang, Zhen Huan, Jindong Yang, Jinpei Cheng. Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3806-3825.

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图/表 42

图式1. X—H键的不同断裂模式

Scheme 1. Scission patterns of X—H bonds

Hydride donor	Thermodynamic hydricity		Kinetic hydricity
Hydride donor	ΔG_H–/(kJ•mol^–1)	Solvent	N	Solvent
NaBH₄	211.0^a	MeCN	14.74	DMSO
Me₃N-BH₃	306.0^a	MeCN	7.97	DCM
PhSiH₃	403.1^a	MeCN	0.06	DCM
Hantzsch ester	257.4	MeCN	9.00	DCM
HMo(CO)₃Cp^*	268.0	MeCN	4.3	DCM
HW(CO)₃Cp	285.0	MeCN	1.7	DCM

表1. 常见负氢试剂的负氢活性

Table 1. Thermodynamic and kinetic hydricity of commonly-used hydride donors

Element	H	B	C	N	O	Si	P
χ_P	2.20	2.04	2.55	3.04	3.44	1.90	2.19
χ_A&R	2.20	2.01	2.50	3.07	3.50	1.74	2.06

表2. Pauling与Allred-Rochow元素电负性标度

Table 2. Pauling and Allred-Rochow’s electronegativity scale

图1. (a)氮杂环磷阳离子NHP+及其(b)轨道结构与(c)常用NHP-H的结构

Figure 1. (a) Diazaphosphenium cation NHP+ with (b) orbital structures and (c)structures of commonly-used NHP-H

图式2. NHP-H的一般合成路线

Scheme 2. General routes for NHP-H synthesis

Hydride donor	Thermodynamic hydricity		Kinetic hydricity
Hydride donor	ΔG_H–/(kJ•mol^–1)	Solvent	N	Solvent
NHP-H1	142.7^a	MeCN	25.54	MeCN
NHP-H2	173.3^a	MeCN	17.68	MeCN
NHP-H3	177.5^a	MeCN	19.85	MeCN
NHP-H4	186.3^a	MeCN	20.93	MeCN
NHP-H6	159.5^a	MeCN	—	—
NHP-H7	198.0^a	MeCN	18.74	MeCN
NHP-H8	204.3^a	MeCN	13.46	MeCN
NHP-H9	260.4	MeCN	8.46	MeCN

表3. NHP-H试剂的热力学与动力学参数

Table 3. Thermodynamic and kinetic hydricity of NHP-H

图式3. NHP-H催化还原反应的一般机理和过渡态

Scheme 3. General mechanism for NHP-H catalysis and the corresponding transition states

图式4. NHP-H作为质子、负氢与氢原子供体

Scheme 4. NHP-H as hydride, hydrogen-atom and proton donors

图式5. NHP-H催化的偶氮苯还原反应

Scheme 5. NHP-H-catalyzed hydrogenation of azobenzenes

图式6. NHP-H催化的醛酮硼氢化还原反应

Scheme 6. NHP-H-catalyzed reduction of aldehydes and ketones

图式7. NHP-H催化的CO2还原反应机理

Scheme 7. Mechanism of NHP-H-catalyzed reduction of CO2

图式8. NHP-H催化CO2对胺的甲酰化和甲基化

Scheme 8. NHP-H-catalyzed N-formylation and methylation of amines by CO2

图式9. [NHP]+与$\mathrm{HCO}_{2}^{-}$的动态平衡

Scheme 9. Dynamic equilibrium of [NHP]+ and $\mathrm{HCO}_{2}^{-}$

图式10. NHP-H催化的α,β-不饱和羰基化合物的还原

Scheme 10. NHP-H-catalyzed reductions of α,β-unsaturated carbonyl compounds

图式11. NHP-H诱导的瞬态磷-烯醇负离子中间体重排反应

Scheme 11. NHP-H-induced rearrangement reactions of transient phosphorus-enolate intermediates

图式12. NHP-H催化的α,β-不饱和羰基化合物不对称还原

Scheme 12. NHP-H-catalyzed chiral reductions of α,β-unsatu- rated carbonyl derivatives

图式13. NHP-H催化还原亚胺

Scheme 13. NHP-H-catalyzed imine reductions

图式14. NHP-H催化的不对称亚胺还原

Scheme 14. Asymmetric reductions of imines catalyzed by NHP-H catalysts a The enantiomer of NHP-6+ was used.

图式15. NHP-H催化的吡啶还原

Scheme 15. NHP-H-catalyzed pyridine reductions

图式16. NHP-H催化的三氟甲基烯烃选择性脱氟氢化反应

Scheme 16. NHP-H-catalyzed selective hydrodefluorination of trifluoromethylalkenes

图式17. NHP-H催化的脱氟氢化机理

Scheme 17. Proposed mechanism for NHP-H-catalyzed hydrodefluorination

图式18. NHP-H催化的多氟芳烃脱氟氢化

Scheme 18. NHP-H-catalyzed hydrodefluorination of polyfluo- roarenes

图式19. 制备NHP自由基和二聚体的方法

Scheme 19. Methods for synthesis of NHP radicals and dimers

图2. (NHP)2的结构

Figure 2. Structure of (NHP)2

图3. (NHP)2的P—P键长(nm)

Figure 3. P—P bond length (nm) of (NHP)2 a Experimental data in Ref. [63]. b Experimental data in Ref. [66]. c Calculated with ωB97X-D in Ref. [66]. d Calculated with M06-2X in Ref. [66].

图4. 353 K下甲苯溶液中(NHP)2的EPR图谱(解离成自由基)

Figure 4. EPR spectrum of (NHP)2 in toluene at 353 K (disso- ciating into radicals)

图5. (NHP)2的解离焓ΔHDiss和解离自由能ΔGDiss

Figure 5. Homolytic bond dissociation free energy changes(ΔGDiss) and bond dissociation enthalpy changes(ΔHDiss) of (NHP)2 a Experimental data in Ref. [69]. b Calculated values with ωB97X-D in Ref. [68]. c Calculated values with M06-2X in Ref. [68].

图式20. NHP-H的热力学循环

Scheme 20. Thermodynamic cycle of NHP-H

图6. NHP-H中P—H键的键解离自由能(BDFE)

Figure 6. P—H BDFEs of NHP-H a Experimental data in Ref. [36]. b Calculated values in Ref. [33].

图式21. NHP自由基的两种反应模式

Scheme 21. Two reaction modes of NHP radicals

图式22. NHP自由基与杂联烯的反应性

Scheme 22. Reactivities of NHP radicals with heteroallenes

图式23. NHP-H催化的自由基还原的机理

Scheme 23. Mechanism for NHP-H-catalyzed radical reduction

图式24. 自由基脱卤氢化反应的条件优化

Scheme 24. Condition optimization for radical hydrodehalogenation

图式25. NHP-H参与的自由基脱卤氢化反应

Scheme 25. NHP-H-mediated radical hydrodehalogenation

图式26. NHP-H参与的自由基脱卤氢化反应的机理

Scheme 26. Mechanism for NHP-H-mediated radical hydrodehalogenation

图式 27. NHP-H参与的自由基环化反应

Scheme 27. NHP-H-mediated radical cyclization

图式28. 亲电试剂对P—P键的官能团化

Scheme 28. Functionalization of P—P bonds with diverse electrophiles

图式29. NHP-H催化的O-乙酰化苯偶姻的C—O键的化学选择性断裂

Scheme 29. NHP-H-catalyzed chemo-selective cleavage of C—O bonds of O-acetylated benzoin

图式30. NHP-H催化的C—O键活化

Scheme 30. NHP-H-catalyzed C—O bond activation

图式31. NHP-H催化的C—O键断裂机理

Scheme 31. Mechanism for NHP-H-catalyzed C—O bond scission

图式32. NHP-H催化的有机卤化物的自由基环化反应

Scheme 32. NHP-H-catalyzed radical cyclization of organohalides

图式33. NHP-H催化的有机卤化物的自由基环化反应的机理

Scheme 33. Proposed mechanism for NHP-H-catalyzed radical cyclization

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氮杂环磷氢试剂的氢转移活性研究进展

Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines

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