均相钴催化氨硼烷的脱氢及转移氢化反应的研究进展

doi:10.6023/cjoc202302020

摘要/Abstract

作为理想的化学储氢材料, 氨硼烷的高效脱氢和转移氢化的研究已经引起了越来越多的重视. 由于丰产金属具有价廉易得和生物兼容性好等优势, 丰产金属均相催化氨基硼烷的脱氢及相关转化, 是该领域的重要发展方向. 主要综述了代表性的均相丰产金属钴络合物催化的氨基硼烷的脱氢和转移氢化的研究进展.

关键词: 氨硼烷, 均相催化, 钴络合物, 脱氢, 转移氢化

As an ideal chemical hydrogen storage material, efficient dehydrogenation and transfer hydrogenation of ammonia borane has attracted increasing attention. Due to the advantages of cheap and easy availability and biocompatibility of earth-abundant metals, the development of homogeneous catalytic dehydrogenation and related transformation of ammonia borane with earth-abundant metals is a significant research topic in this field. Herein, the development of dehydrogenation and transfer hydrogenation of ammonia borane catalyzed by homogeneous cobalt complexes is reviewed.

Key words: ammonia borane, homogeneous catalysis, cobalt complex, dehydrogenation, transfer hydrogenation

引用此文

刘双, 邹亮华, 王晓明. 均相钴催化氨硼烷的脱氢及转移氢化反应的研究进展[J]. 有机化学, 2023, 43(5): 1713-1725.

Shuang Liu, Lianghua Zou, Xiaoming Wang. Advance of Dehydrogenation and Transfer Hydrogenation of Ammonia-Borane Catalyzed by Homogeneous Cobalt Complexes[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1713-1725.

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图/表 16

图1. 代表性的氨硼烷脱氢的钴络合物催化剂

Figure 1. Representative homogeneous cobalt catalysts for amine-borane dehydrogenation

图式1. PBP-CoI(N2) 1和1'的合成及催化DMAB的脱氢

Scheme 1. Synthesis of PBP-CoI(N2) 1 and 1' and their application in catalytic DMAB dehydrogenation

图式2. 推测的PBP-Co(N2)催化氨硼烷脱氢催化循环

Scheme 2. Proposed catalytic cycle for catalytic AB dehydrogenation with PBP-Co(N2)

图式3. 络合物(MesCCC)CoH(NH2BH3)的合成

Scheme 3. Synthesis of complex (MesCCC)CoH(NH2BH3)

图式4. 钴催化的炔烃立体发散性半氢化

Scheme 4. Stereodivergent hydrogenation of alkyne by cobalt catalysts

图式5. NNN-Co催化炔烃的Z-转移氢化和控制实验

Scheme 5. NNN-Co catalyzed Z-transfer hydrogenation of alkyne and controlled experiment

图式6. Pyridonate-钴协同催化末端炔串联转化为(E,Z)-1,3-二烯

Scheme 6. Sequential transformation of terminal alkynes to (E,Z)-1,3-dienes by a cooperative pyridonate-cobalt catalyst

图式7. κ2-(QNN)CoBr2(NC(O)HNEt2)催化炔烃的Z-转移氢化

Scheme 7. κ2-(QNN)CoBr2(NC(O)HNEt2) catalyzed Z-transfer hydrogenation of alkyne

图式8. PNNH-Co催化炔烃的E-转移氢化

Scheme 8. E-Transfer hydrogenation of alkyne by PNNH-Co catalysis

图式9. (N4)-Co催化烯烃的转移氢化

Scheme 9. Transfer hydrogenation of alkene by (N4)-Co catalysis

图式10. PNN-Co催化腈的化学发散性转移氢化反应

Scheme 10. PNN-Co catalyzed chemo-divergent transfer hydrogenation of nitriles

图式11. [ArBIAN-Co(η4-cod)]–[K(thf)x]+催化氨硼烷转移氢化

Scheme 11. [ArBIAN-Co(η4-cod)]–[K(thf)x]+ catalyzed transfer hydrogenation of ammonia borane

图式12. Xantphos-Co催化腈生成仲胺和叔胺

Scheme 12. Xantphos-Co catalyzed reductions of nitriles to secondary and tertiary amines

图式13. 铒催化的区域选择性异构化-钴催化转移氢化

Scheme 13. Erbium-catalyzed regioselective isomerization-cobalt-catalyzed transfer hydrogenation

图式14. 钴-胺协同催化喹啉可控的部分转移氢化

Scheme 14. Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis

图式15. 钴-胺协同催化吡啶的选择性去芳构化生成N—H 1,4-二氢吡啶

Scheme 15. Selective dearomatization of pyridines to N—H 1,4-dihydropyridines by cobalt-amido cooperative catalysis

参考文献 36

[1]	(a) Filippov, S. P.; Yaroslavtsev, A. B. Russ. Chem. Rev. 2021, 90, 627. doi: 10.1070/RCR5014
	(b) Wang, D.; Astruc, D. Chem. Rev. 2015, 115, 6621. doi: 10.1021/acs.chemrev.5b00203
	(c) He, Y.; Wang, D. Chem 2018, 4, 405. doi: 10.1016/j.chempr.2018.02.013
	(d) Midilli, A.; Ay, M.; Dincer, I.; Rosen, M. A. Renew. Sust. Energ. Rev. 2005, 9, 255. doi: 10.1016/j.rser.2004.05.003
[2]	(a) Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079. doi: 10.1021/cr100088b pmid: 27174725
	(b) Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023. doi: 10.1021/cr100105a pmid: 27174725
	(c) Stephens, F. H.; Pons, V.; Tom Baker, R. Dalton Trans. 2007, 2613. pmid: 27174725
	(d) Zou, S.-S.; Tao, Z.-L.; Chen, J. Acta Chim. Sinica 2011, 69, 2117. (in Chinese) pmid: 27174725
	(邹少爽, 陶占良, 陈军, 化学学报, 2011, 69, 2117.) pmid: 27174725
	(e) Ganguly, G.; Malakar, T.; Paul, A. ChemSusChem 2016, 9, 1386. doi: 10.1002/cssc.201600213 pmid: 27174725
	(f) Bhattacharjee, I.; Sultana, M.; Bhunya, S.; Paul, A. Chem. Commun. 2022, 58, 1672. doi: 10.1039/D1CC06238G pmid: 27174725
[3]	(a) Bhunya, S.; Malakar, T.; Ganguly, G.; Paul, A. ACS Catal. 2016, 6, 7907. doi: 10.1021/acscatal.6b01704
	(b) Faverio, C.; Boselli, M. F.; Medici, F.; Benaglia, M. Org. Biomol. Chem. 2020, 18, 7789. doi: 10.1039/D0OB01351J
	(c) Lau, S.; Gasperini, D.; Webster, R. L. Angew. Chem., Int. Ed. 2021, 60, 14272. doi: 10.1002/anie.v60.26
	(d) Rossin, A.; Peruzzini, M. Chem. Rev. 2016, 116, 8848. doi: 10.1021/acs.chemrev.6b00043
	(e) Yang, X.; Xie, Z.; He, J.; Yu, L. Chin. J. Org. Chem. 2015, 35, 603. (in Chinese) doi: 10.6023/cjoc201412057
	(阳香华, 谢珍茗, 何军, 余林, 有机化学, 2015, 35, 603.) doi: 10.6023/cjoc201412057
	(f) Alig, L.; Fritz, M.; Schneider, S. Chem. Rev. 2019, 119, 2681. doi: 10.1021/acs.chemrev.8b00555
	(g) Sharma, D. M.; Punji, B. Chem. Asian J. 2020, 15, 690. doi: 10.1002/asia.v15.6
	(h) Liu, X.; Zhang, W.; Wang, Y.; Zhang, Z.-X.; Jiao, L.; Liu, Q. J. Am. Chem. Soc. 2018, 140, 6873. doi: 10.1021/jacs.8b01815
	(i) Zhang, S.; Bedi, D.; Cheng, L.; Unruh, D. K.; Li, G.; Findlater, M. J. Am. Chem. Soc. 2020, 142, 8910. doi: 10.1021/jacs.0c02101
	(j) Stevens, M. A.; Colebatch, A. L. Chem. Soc. Rev. 2022, 51, 1881. doi: 10.1039/D1CS01171E
[4]	Shore, S. G.; Parry, R. W. J. Am. Chem. Soc. 1955, 77, 6084. doi: 10.1021/ja01627a103
[5]	Blaquiere, N.; Diallo-Garcia, S.; Gorelsky, S. I.; Black, D. A.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 14034. doi: 10.1021/ja804235t pmid: 18831582
[6]	(a) Conley, B. L.; Williams, T. J. Chem. Commun. 2010, 46, 4815. doi: 10.1039/c003157g
	(b) Lu, Z.; Conley, B. L.; Williams, T. J. Organometallics 2012, 31, 6705. doi: 10.1021/om300562d
	(c) Zhang, X.; Lu, Z.; Foellmer, L. K.; Williams, T. J. Organometallics 2015, 34, 3732. doi: 10.1021/acs.organomet.5b00409
	(d) Zhang, X.; Kam, L.; Trerise, R.; Williams, T. J. Acc. Chem. Res. 2017, 50, 86. doi: 10.1021/acs.accounts.6b00482
[7]	(a) Tang, C. Y.; Thompson, A. L.; Aldridge, S. J. Am. Chem. Soc. 2010, 132, 10578. doi: 10.1021/ja1043787
	(b) Tang, C. Y.; Thompson, A. L.; Aldridge, S. Angew. Chem., Int. Ed. 2010, 49, 921. doi: 10.1002/anie.200906171
	(c) Tang, C. Y.; Phillips, N.; Bates, J. I.; Thompson, A. L.; Gutmann, M. J.; Aldridge, S. Chem. Commun. 2012, 48, 8096. doi: 10.1039/c2cc33361a
[8]	(a) Johnson, H. C.; Robertson, A. P.; Chaplin, A. B.; Sewell, L. J.; Thompson, A. L.; Haddow, M. F.; Manners, I.; Weller, A. S. J. Am. Chem. Soc. 2011, 133, 11076. doi: 10.1021/ja2040738
	(b) Stevens, C. J.; Dallanegra, R.; Chaplin, A. B.; Weller, A. S.; Macgregor, S. A.; Ward, B.; McKay, D.; Alcaraz, G.; Sabo-Etienne, S. Chem.-Eur. J. 2011, 17, 3011. doi: 10.1002/chem.v17.10
	(c) Kumar, A.; Johnson, H. C.; Hooper, T. N.; Weller, A. S.; Algarra, A. G.; Macgregor, S. A. Chem. Sci. 2014, 5, 2546. doi: 10.1039/C4SC00735B
[9]	Kim, S.-K.; Han, W.-S.; Kim, T.-J.; Kim, T.-Y.; Nam, S. W.; Mitoraj, M.; Piekoś, Ł.; Michalak, A.; Hwang, S.-J.; Kang, S. O. J. Am. Chem. Soc. 2010, 132, 9954. doi: 10.1021/ja101685u
[10]	Rosello-Merino, M.; Lopez-Serrano, J.; Conejero, S. J. Am. Chem. Soc. 2013, 135, 10910. doi: 10.1021/ja404655v
[11]	Lin, T.-P.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 15310. doi: 10.1021/ja408397v
[12]	Ganguly, G.; Malakar, T.; Paul, A. ACS Catal. 2015, 5, 2754. doi: 10.1021/cs501359n
[13]	Pagano, J. K.; Stelmach, J. P.; Waterman, R. Dalton Trans. 2015, 44, 12074. doi: 10.1039/C5DT00108K
[14]	Todisco, S.; Luconi, L.; Giambastiani, G.; Rossin, A.; Peruzzini, M.; Golub, I. E.; Filippov, O. A.; Belkova, N. V.; Shubina, E. S. Inorg. Chem. 2017, 56, 4296. doi: 10.1021/acs.inorgchem.6b02673
[15]	Maier, T. M.; Sandl, S.; Shenderovich, I. G.; Jacobi von Wangelin, A.; Weigand, J. J.; Wolf, R. Chem.-Eur. J. 2019, 25, 238. doi: 10.1002/chem.v25.1
[16]	Boyd, T. M.; Andrea, K. A.; Baston, K.; Johnson, A.; Ryan, D. E.; Weller, A. S. Chem. Commun. 2020, 56, 482. doi: 10.1039/C9CC08864D
[17]	Nugent, J. W.; García-Melchor, M.; Fout, A. R. Organometallics 2020, 39, 2917. doi: 10.1021/acs.organomet.0c00459
[18]	Jiang, Y.; Blacque, O.; Fox, T.; Frech, C. M.; Berke, H. Organometallics 2009, 28, 5493. doi: 10.1021/om900458e
[19]	Hartmann, C. E.; Jurcik, V.; Songis, O.; Cazin, C. S. Chem. Commun. 2013, 49, 1005. doi: 10.1039/C2CC38145A
[20]	Gelis, C.; Heusler, A.; Nairoukh, Z.; Glorius, F. Chem.-Eur. J. 2020, 26, 14090. doi: 10.1002/chem.v26.62
[21]	Wang, L.; Lin, J.; Xia, C.; Sun, W. J. Catal. 2022, 413, 487. doi: 10.1016/j.jcat.2022.06.045
[22]	Vermaak, V.; Vosloo, H. C. M.; Swarts, A. J. Adv. Synth. Catal. 2020, 362, 5788. doi: 10.1002/adsc.v362.24
[23]	(a) Ai, W.; Zhong, R.; Liu, X.; Liu, Q. Chem. Rev. 2019, 119, 2876. doi: 10.1021/acs.chemrev.8b00404
	(b) Wang, M.; Shi, Z. Chem. Rev. 2020, 120, 7348. doi: 10.1021/acs.chemrev.9b00384
	(c) Raya, B.; Jing, S.; RajanBabu, T. V. ACS Catal. 2017, 7, 2275. doi: 10.1021/acscatal.6b03373
	(d) Du, X.; Xiao, Y.; Huang, J. M.; Zhang, Y.; Duan, Y. N.; Wang, H.; Shi, C.; Chen, G. Q.; Zhang, X. Nat. Commun. 2020, 11, 3239. doi: 10.1038/s41467-020-17057-z
	(e) Wang, D.; Lai, Y.; Wang, P.; Leng, X.; Xiao, J.; Deng, L. J. Am. Chem. Soc. 2021, 143, 12847. doi: 10.1021/jacs.1c06583
	(f) Chen, K.; Zhu, H.; Li, Y.; Peng, Q.; Guo, Y.; Wang, X. ACS Catal. 2021, 11, 13696. doi: 10.1021/acscatal.1c04141
[24]	(a) Wang, D. S.; Chen, Q. A.; Lu, S. M.; Zhou, Y. G. Chem. Rev. 2012, 112, 2557. doi: 10.1021/cr200328h pmid: 27709917
	(b) Oger, C.; Balas, L.; Durand, T.; Galano, J. M. Chem. Rev. 2013, 113, 1313. doi: 10.1021/cr3001753 pmid: 27709917
	(c) Chinchilla, R.; Najera, C. Chem. Rev. 2014, 114, 1783. doi: 10.1021/cr400133p pmid: 27709917
	(d) Meemken, F.; Baiker, A. Chem. Rev. 2017, 117, 11522. doi: 10.1021/acs.chemrev.7b00272 pmid: 27709917
	(e) Tokmic, K.; Fout, A. R. J. Am. Chem. Soc. 2016, 138, 13700. doi: 10.1021/jacs.6b08128 pmid: 27709917
	(f) Gorgas, N.; Brunig, J.; Stoger, B.; Vanicek, S.; Tilset, M.; Veiros, L. F.; Kirchner, K. J. Am. Chem. Soc. 2019, 141, 17452. doi: 10.1021/jacs.9b09907 pmid: 27709917
	(g) Kim, A. N.; Stoltz, B. M. ACS Catal. 2020, 10, 13834. doi: 10.1021/acscatal.0c03958 pmid: 27709917
[25]	Fu, S.; Chen, N.-Y.; Liu, X.; Shao, Z.; Luo, S.-P.; Liu, Q. J. Am. Chem. Soc. 2016, 138, 8588. doi: 10.1021/jacs.6b04271
[26]	Landge, V. G.; Pitchaimani, J.; Midya, S. P.; Subaramanian, M.; Madhu, V.; Balaraman, E. Catal. Sci. Technol. 2018, 8, 428. doi: 10.1039/C7CY01994G
[27]	Zhuang, X.; Chen, J.-Y.; Yang, Z.; Jia, M.; Wu, C.; Liao, R.-Z.; Tung, C.-H.; Wang, W. Organometallics 2019, 38, 3752. doi: 10.1021/acs.organomet.9b00486
[28]	Sharma, D. M.; Gouda, C.; Gonnade, R. G.; Punji, B. Catal. Sci. Technol. 2022, 12, 1843. doi: 10.1039/D2CY00027J
[29]	Decker, D.; Wei, Z.; Rabeah, J.; Drexler, H.-J.; Brückner, A.; Jiao, H.; Beweries, T. Inorg. Chem. Front. 2022, 9, 761. doi: 10.1039/D1QI00998B
[30]	Tian, J.; Xu, D.; Sun, W. Adv. Synth. Catal. 2022, 364, 3874. doi: 10.1002/adsc.v364.22
[31]	(a) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471. pmid: 31791120
	(b) Sridharan, V.; Suryavanshi, P. A.; Menendez, J. C. Chem. Rev. 2011, 111, 7157. doi: 10.1021/cr100307m pmid: 31791120
	(c) Malacea, R.; Poli, R.; Manoury, E. Coord. Chem. Rev. 2010, 254, 729. doi: 10.1016/j.ccr.2009.09.033 pmid: 31791120
	(d) Korstanje, T. J.; Ivar van der Vlugt, J.; Elsevier, C. J.; de Bruin, B. Science 2015, 350, 298. pmid: 31791120
	(e) Duan, Y. N.; Du, X.; Cui, Z.; Zeng, Y.; Liu, Y.; Yang, T.; Wen, J.; Zhang, X. J. Am. Chem. Soc. 2019, 141, 20424. doi: 10.1021/jacs.9b11070 pmid: 31791120
	(f) Gao, C.; Xuan, Q.; Song, Q. Chin. J. Chem. 2021, 39, 2504. doi: 10.1002/cjoc.v39.9 pmid: 31791120
[32]	Shao, Z.; Fu, S.; Wei, M.; Zhou, S.; Liu, Q. Angew. Chem., Int. Ed. 2016, 55, 14653. doi: 10.1002/anie.v55.47
[33]	Sharma, D. M.; Punji, B. Adv. Synth. Catal. 2019, 361, 3930. doi: 10.1002/adsc.v361.17
[34]	Liu, X.; Longwitz, L.; Spiegelberg, B.; Tönjes, J.; Beweries, T.; Werner, T. ACS Catal. 2020, 10, 13659. doi: 10.1021/acscatal.0c03294
[35]	Pang, M.; Chen, J.-Y.; Zhang, S.; Liao, R.-Z.; Tung, C.-H.; Wang, W. Nat. Commun. 2020, 11, 1249. doi: 10.1038/s41467-020-15118-x
[36]	Pang, M.; Shi, L.-L.; Xie, Y.; Geng, T.; Liu, L.; Liao, R.-Z.; Tung, C.-H.; Wang, W. ACS Catal. 2022, 12, 5013. doi: 10.1021/acscatal.2c00271