Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines

doi:10.6023/cjoc202304023

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3806-3825.DOI: 10.6023/cjoc202304023 Previous Articles Next Articles

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

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

Cite this article

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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Fig. & Tab. 42

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

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

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

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

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

Table 3. Thermodynamic and kinetic hydricity of NHP-H

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

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

Scheme 5. NHP-H-catalyzed hydrogenation of azobenzenes

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

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

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

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

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

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

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

Scheme 13. NHP-H-catalyzed imine reductions

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

Scheme 15. NHP-H-catalyzed pyridine reductions

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

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

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

Scheme 19. Methods for synthesis of NHP radicals and dimers

Figure 2. Structure of (NHP)2

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].

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

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].

Scheme 20. Thermodynamic cycle of NHP-H

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

Scheme 21. Two reaction modes of NHP radicals

Scheme 22. Reactivities of NHP radicals with heteroallenes

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

Scheme 24. Condition optimization for radical hydrodehalogenation

Scheme 25. NHP-H-mediated radical hydrodehalogenation

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

Scheme 27. NHP-H-mediated radical cyclization

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

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

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

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

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

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

References 75

[1]	Ai, W.; Zhong, R.; Liu, X.; Liu, Q. Chem. Rev. 2019, 119, 2876. doi: 10.1021/acs.chemrev.8b00404
[2]	Jordan, A. J.; Lalic, G.; Sadighi, J. P. Chem. Rev. 2016, 116, 8318. doi: 10.1021/acs.chemrev.6b00366
[3]	Roy, M. M. D.; Omaña, A. A.; Wilson, A. S. S.; Hill, M. S.; Aldridge, S.; Rivard, E. Chem. Rev. 2021, 121, 12784. doi: 10.1021/acs.chemrev.1c00278
[4]	McGrady, G. S.; Guilera, G. Chem. Soc. Rev. 2003, 32, 383. doi: 10.1039/b207999m pmid: 14671793
[5]	Aldridge, S.; Downs, A. J. Chem. Rev. 2001, 101, 3305. pmid: 11840988
[6]	Ilic, S.; Alherz, A.; Musgrave, C. B.; Glusac, K. D. Chem. Soc. Rev. 2018, 47, 2809. doi: 10.1039/C7CS00171A
[7]	Mayr, H.; Patz, M. Angew. Chem., Int. Ed. 1994, 33, 938. doi: 10.1002/anie.v33:9
[8]	Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500. pmid: 11572670
[9]	Wiedner, E. S.; Chambers, M. B.; Pitman, C. L.; Bullock, R. M.; Miller, A. J.; Appel, A. M. Chem. Rev. 2016, 116, 8655. doi: 10.1021/acs.chemrev.6b00168 pmid: 27483171
[10]	Brereton, K. R.; Smith, N. E.; Hazari, N.; Miller, A. J. M. Chem. Soc. Rev. 2020, 49, 7929. doi: 10.1039/D0CS00405G
[11]	Heiden, Z. M.; Lathem, A. P. Organometallics 2015, 34, 1818. doi: 10.1021/om5011512
[12]	Sarker, N.; Bruno, J. W. J. Am. Chem. Soc. 1999, 121, 2174. doi: 10.1021/ja982017b
[13]	Ciancanelli, R.; Noll, B. C.; DuBois, D. L.; DuBois, M. R. J. Am. Chem. Soc. 2002, 124, 2984. pmid: 11902890
[14]	Estes, D. P.; Vannucci, A. K.; Hall, A. R.; Lichtenberger, D. L.; Norton, J. R. Organometallics 2011, 30, 3444. doi: 10.1021/om2001519
[15]	Hu, Y.; Norton, J. R. J. Am. Chem. Soc. 2014, 136, 5938. doi: 10.1021/ja412309j
[16]	Horn, M.; Schappele, L. H.; Lang-Wittkowski, G.; Mayr, H.; Ofial, A. R. Chem.-Eur. J. 2013, 19, 249. doi: 10.1002/chem.v19.1
[17]	Longeau, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 6099. doi: 10.1016/0040-4039(96)01296-8
[18]	Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012. doi: 10.1021/ja0555163
[19]	Blum, M.; Kappler, J.; Schlindwein, S. H.; Nieger, M.; Gudat, D. Dalton Trans. 2018, 47, 112. doi: 10.1039/C7DT04110A
[20]	Leca, D.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858. doi: 10.1039/b500511f
[21]	Marque, S.; Tordo, P. Top. Curr. Chem. 2005, 250, 43.
[22]	Gao, Y.; Tang, G.; Zhao, Y. Chin. J. Org. Chem. 2018, 38, 62. (in Chinese) doi: 10.6023/cjoc201708023
	(高玉珍, 唐果, 赵玉芬, 有机化学, 2018, 38, 62.) doi: 10.6023/cjoc201708023
[23]	Bezombes, J.-P.; Carré, F.; Chuit, C.; Corriu, R. J. P.; Mehdi, A.; Reyé, C. J. Org. Chem. 1997, 535, 81.
[24]	Carré, F.; Chuit, C.; Corriu, R. J. P.; Mehdi, A.; Reyé, C. J. Org. Chem. 1997, 529, 59.
[25]	Gudat, D.; Haghverdi, A.; Nieger, M. Angew. Chem., Int. Ed. 2000, 39, 3084. doi: 10.1002/(ISSN)1521-3773
[26]	Fleming, S.; Lupton, M. K.; Jekot, K. Inorg. Chem. 1972, 11, 2534. doi: 10.1021/ic50116a050
[27]	Maryanoff, B. E.; Hutchins, R. O. J. Org. Chem 1972, 37, 3475. doi: 10.1021/jo00795a018
[28]	Karaghiosoff, K.; Majoral, J. P.; Meriem, A.; Navech, J.; Schmid- peter, A. Tetrahedron Lett. 1983, 24, 2137. doi: 10.1016/S0040-4039(00)81864-X
[29]	Kibardin, A. M.; Mikhailov, Y. B.; Gryaznova, T. V.; Pudovik, A. N. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986, 35, 878. doi: 10.1007/BF00954265
[30]	Jennings, W. B.; Randall, D.; Worley, S. D.; Hargis, J. H. J. Chem. Soc., Perkin Trans. II 1981, 1411.
[31]	Dube, J. W.; Farrar, G. J.; Norton, E. L.; Szekely, K. L. S.; Cooper, B. F. T.; Macdonald, C. L. B. Organometallics 2009, 28, 4377. doi: 10.1021/om900420g
[32]	Burck, S.; Gudat, D.; Nieger, M.; Du Mont, W.-W. J. Am. Chem. Soc. 2006, 128, 3946. doi: 10.1021/ja057827j
[33]	Alkhater, M. F.; Alherz, A. W.; Musgrave, C. B. Phys. Chem. Chem. Phys. 2021, 23, 17794. doi: 10.1039/D1CP02193A
[34]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Angew. Chem., Int. Ed. 2019, 58, 5983. doi: 10.1002/anie.v58.18
[35]	Liu, L. L.; Wu, Y.; Chen, P.; Chan, C.; Xu, J.; Zhu, J.; Zhao, Y. Org. Chem. Front. 2016, 3, 423. doi: 10.1039/C6QO00002A
[36]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Chem. Sci. 2020, 11, 3672. doi: 10.1039/C9SC05883D
[37]	Chong, C. C.; Hirao, H.; Kinjo, R. Angew. Chem., Int. Ed. 2014, 53, 3342. doi: 10.1002/anie.v53.13
[38]	Waterman, R. Organometallics 2013, 32, 7249. doi: 10.1021/om400760k
[39]	Chong, C. C.; Hirao, H.; Kinjo, R. Angew. Chem., Int. Ed. 2015, 54, 190. doi: 10.1002/anie.v54.1
[40]	Edge, R.; Less, R. J.; McInnes, E. J. L.; Müther, K.; Naseri, V.; Rawson, J. M.; Wright, D. S. Chem. Commun. 2009, 1691.
[41]	Gudat, D. Dalton Trans. 2016, 45, 5896. doi: 10.1039/c6dt00085a pmid: 26863391
[42]	Ould, D. M. C.; Melen, R. L. Chem.-Eur. J. 2020, 26, 9835. doi: 10.1002/chem.v26.44
[43]	Speed, A. W. H. Chem. Soc. Rev. 2020, 49, 8335. doi: 10.1039/D0CS00476F
[44]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Natl. Sci. Rev. 2021, 8, nwaa253. doi: 10.1093/nsr/nwaa253
[45]	Zhang, Y.-S.; Huan, Z.; Yang, J.-D.; Cheng, J.-P. Chem. Commun. 2022, 58, 12528. doi: 10.1039/D2CC04844B
[46]	Ould, D. M. C.; Tran, T. T. P.; Rawson, J. M.; Melen, R. L. Dalton Trans. 2019, 48, 16922. doi: 10.1039/C9DT03577J
[47]	Chong, C. C.; Kinjo, R. Angew. Chem., Int. Ed. 2015, 54, 12116. doi: 10.1002/anie.v54.41
[48]	Lu, Y.; Gao, Z. H.; Chen, X. Y.; Guo, J.; Liu, Z.; Dang, Y.; Ye, S.; Wang, Z. X. Chem. Sci. 2017, 8, 7637. doi: 10.1039/C7SC00824D
[49]	Adams, M. R.; Tien, C. H.; Huchenski, B. S. N.; Ferguson, M. J.; Speed, A. W. H. Angew. Chem., Int. Ed. 2017, 56, 6268. doi: 10.1002/anie.v56.22
[50]	Chong, C. C.; Rao, B.; Kinjo, R. ACS Catal. 2017, 7, 5814. doi: 10.1021/acscatal.7b01338
[51]	Reed, J. H.; Cramer, N. ChemCatChem 2020, 12, 4262. doi: 10.1002/cctc.v12.17
[52]	Reed, J. H.; Donets, P. A.; Miaskiewicz, S.; Cramer, N. Angew. Chem., Int. Ed. 2019, 58, 8893. doi: 10.1002/anie.v58.26
[53]	Zhang, G.; Cramer, N. Angew. Chem., Int. Ed. 2023, 62, e202301076. doi: 10.1002/anie.v62.17
[54]	Miaskiewicz, S.; Reed, J. H.; Donets, P. A.; Oliveira, C. C.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 4039. doi: 10.1002/anie.v57.15
[55]	Lin, Y. C.; Hatzakis, E.; McCarthy, S. M.; Reichl, K. D.; Lai, T. Y.; Yennawar, H. P.; Radosevich, A. T. J. Am. Chem. Soc. 2017, 139, 6008. doi: 10.1021/jacs.7b02512
[56]	Adams, M. R.; Tien, C. H.; McDonald, R.; Speed, A. W. H. Angew. Chem., Int. Ed. 2017, 56, 16660. doi: 10.1002/anie.v56.52
[57]	Rao, B.; Chong, C. C.; Kinjo, R. J. Am. Chem. Soc. 2018, 140, 652. doi: 10.1021/jacs.7b09754
[58]	Lundrigan, T.; Welsh, E. N.; Hynes, T.; Tien, C. H.; Adams, M. R.; Roy, K. R.; Robertson, K. N.; Speed, A. W. H. J. Am. Chem. Soc. 2019, 141, 14083. doi: 10.1021/jacs.9b07293 pmid: 31441650
[59]	Lundrigan, T.; Tien, C. H.; Robertson, K. N.; Speed, A. W. H. Chem. Commun. 2020, 56, 8027. doi: 10.1039/D0CC01072C
[60]	Hynes, T.; Welsh, E. N.; McDonald, R.; Ferguson, M. J.; Speed, A. W. H. Organometallics 2018, 37, 841. doi: 10.1021/acs.organomet.8b00028
[61]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Nat. Commun. 2021, 12, 2835. doi: 10.1038/s41467-021-23101-3
[62]	Zhang, J.; Zhao, X.; Yang, J.-D.; Cheng, J.-P. J. Org. Chem. 2022, 87, 294. doi: 10.1021/acs.joc.1c02360
[63]	Puntigam, O.; Förster, D.; Giffin, N. A.; Burck, S.; Bender, J.; Ehret, F.; Hendsbee, A. D.; Nieger, M.; Masuda, J. D.; Gudat, D. Eur. J. Inorg. Chem. 2013, 2041.
[64]	Burck, S.; Gudat, D.; Nieger, M. Angew. Chem., Int. Ed. 2004, 43, 4801. doi: 10.1002/anie.v43:36
[65]	Burck, S.; Götz, K.; Kaupp, M.; Nieger, M.; Weber, J.; Schmedt auf der Günne, J.; Gudat, D. J. Am. Chem. Soc. 2009, 131, 10763. doi: 10.1021/ja903156p
[66]	Ma, M.; Shen, L.; Wang, H.; Zhao, Y.; Wu, B.; Yang, X.-J. Organometallics 2020, 39, 1440. doi: 10.1021/acs.organomet.0c00136
[67]	Abakumov, G. A.; Druzhkov, N. O.; Kazakov, G. G.; Fukin, G. K.; Rumyantsev, R. V.; Cherkasov, V. K. Dokl. Chem. 2019, 489, 279. doi: 10.1134/S0012500819120012
[68]	Förster, D.; Dilger, H.; Ehret, F.; Nieger, M.; Gudat, D. Eur. J. Inorg. Chem. 2012, 3989.
[69]	Blum, M.; Puntigam, O.; Plebst, S.; Ehret, F.; Bender, J.; Nieger, M.; Gudat, D. Dalton Trans. 2016, 45, 1987. doi: 10.1039/c5dt02854j pmid: 26337501
[70]	Giffin, N. A.; Hendsbee, A. D.; Masuda, J. D. Dalton Trans. 2016, 45, 12636. doi: 10.1039/c6dt02790c pmid: 27443569
[71]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Chem. Sci. 2020, 11, 4786. doi: 10.1039/D0SC01352H
[72]	Huchenski, B. S. N.; Robertson, K. N.; Speed, A. W. H. Eur. J. Org. Chem. 2020, 5140.
[73]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Chem. Sci. 2020, 11, 8476. doi: 10.1039/D0SC03220D
[74]	Klett, J.; Wozniak, L.; Cramer, N. Angew. Chem., Int. Ed. 2022, 134, e202202306. doi: 10.1002/ange.v134.30
[75]	Riley, R. D.; Huchenski, B. S. N.; Bamford, K. L.; Speed, A. W. H. Angew. Chem., Int. Ed. 2022, 134, e202204088. doi: 10.1002/ange.v134.30

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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