过渡金属催化的内烯烃不对称硼氢化

doi:10.6023/cjoc202207040

摘要/Abstract

金属催化的烯烃不对称硼氢化是构建手性硼酸酯最为有效的方法之一, 具有原料简单易得、原子经济性高、硼化产物结构多样等特点, 受到化学家的广泛关注. 总结了过渡金属催化的内烯烃的不对称硼氢化, 包括张力环状内烯烃、苯乙烯类内烯烃及含配位基团的内烯烃.

关键词: 硼氢化, 不对称催化, 内烯烃, 硼酸酯

Transition metal catalyzed asymmetric hydroboration of alkenes is one of the most powerful methods to prepare chiral organoboronates, which has attracted extensive attention of chemists due to its simple raw materials, high atomic economy, diverse structure of borated products, etc. The transition metal catalyzed enantioselective hydroboration of internal alkenes including strained internal alkene, β-substituted styrenes and internal alkenes bearing a coordinating group is summarized.

Key words: hydroboration, asymmetric catalysis, internal alkene, organoboronate

引用此文

陆候祥, 李必杰. 过渡金属催化的内烯烃不对称硼氢化[J]. 有机化学, 2022, 42(10): 3167-3182.

Houxiang Lu, Bijie Li. Transition Metal Catalyzed Asymmetric Hydroboration of Internal Alkenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3167-3182.

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图/表 24

图式1. 降冰片烯不对称硼氢化早期研究中的配体

Scheme 1. Ligands of norbornene asymmetric hydroboration in earlier studies

图式2. 双环肼类化合物的不对称硼氢化

Scheme 2. Asymmetric hydroboration of meso-bicyclic hydrazines

图式3. 双环肼类化合物不对称硼氢化的有效单齿配体

Scheme 3. Effective monodentate ligands of asymmetric hydroboration of meso-bicyclic hydrazines

图式4. 铜催化降冰片烯的不对称硼氢化

Scheme 4. Cu catalyzed asymmetric hydroboration of norbornenes

图式5. 铑催化环丙烯的不对称硼氢化

Scheme 5. Rh catalyzed asymmetric hydroboration of cyclopropenes

图式6. 早期金属催化的β-取代苯乙烯不对称硼氢化

Scheme 6. Earlier studies of metal catalyzed asymmetric hydroboration of β-substituted styrenes

图式7. 铑催化的环状苯乙烯类的不对称硼氢化

Scheme 7. Rh catalyzed asymmetric hydroboration of cyclic styrene-type olefins

图式8. β-硼酸酯取代的苯乙烯类不对称硼氢化

Scheme 8. Asymmetric hydroboration of β-boronic ester substituted styrenes

图式9. 铜催化的β-取代苯乙烯的不对称硼氢化

Scheme 9. Cu catalyzed asymmetric hydroboration of β-substituted styrenes

图式10. 铜催化的肉桂醛类的不对称硼氢化

Scheme 10. Cu catalyzed asymmetric hydroboration of cinnamaldehydes

图式11. 钴催化的β-取代苯乙烯的不对称硼氢化

Scheme 11. Co catalyzed asymmetric hydroboration of β-substituted styrenes

图式12. 配位基团导向的环状烯烃非对映选择性硼氢化

Scheme 12. Diastereoselective hydroboration of cyclo-olefins directed by coordinating groups

图式13. 酰胺导向的远端烯烃不对称硼氢化

Scheme 13. Amide directed asymmetric hydroboration of distal alkenes

图式14. 配位基团导向的远端烯烃不对称硼氢化

Scheme 14. Asymmetric hydroboration of distal alkenes directed by coordinating group

图式15. 铑催化的配位基团导向的三取代烯烃不对称硼氢化

Scheme 15. Rh catalyzed asymmetric hydroboration of trisubstituted alkenes directed by coordinating groups

图式16. 铑催化烯丙基酰胺类不对称硼氢化

Scheme 16. Rh catalyzed asymmetric hydroboration of allyl amides

图式17. 铜催化的非活化内烯烃不对称硼氢化

Scheme 17. Cu catalyzed asymmetric hydroboration of non-activated internal olefins

图式18. 铑催化的NHC硼烷分子内不对称硼氢化

Scheme 18. Rh catalyzed NHC-borane intramolecular asymmetric hydroboration

图19. 铜催化的β-硼基苯乙烯不对称硼氢化

Scheme 19. Cu catalyzed asymmetric hydroboration of β-boryl styrene

图式20. 铑催化的烯基酰胺的不对称硼氢化

Scheme 20. Rh catalyzed asymmetric hydroboration of enamides

图式21. 铑催化的醛基烯醇硅醚的不对称硼氢化

Scheme 21. Rh catalyzed asymmetric hydroboration of silyl enol ethers

图式22. 钴催化的端炔不对称硅氢化串联硼氢化

Scheme 22. Co catalyzed asymmetric cascade hydrosilylation-hydroboration of terminal alkynes

图式23. 铑催化的α,β-不饱和酰胺的不对称硼反向硼氢化

Scheme 23. Rh catalyzed asymmetric reversed hydroboration of α,β-unsaturated amides

图式24. 铑催化的β,β-二取代α,β-不饱和酰胺的不对称硼氢化

Scheme 24. Rh catalyzed asymmetric hydroboration of β,β-disubstituted α,β-unsaturated amides

参考文献 24

[1]	Brown, H. C.; Kramer, G. W.; Levy, A. B.; Middland, M. M. Organic Synthesis via Boranes, Wiley-Interscience, New York, 1975. pmid: 22519511
	(b) Hall, D. G., Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed., Wiley-VCH, Weinheim, Germany, 2011. pmid: 22519511
	(c) Neeve, E. C.; Geier, S. J.; Mkhalid, I. A. I.; Westcott, S. A.; Marder, T. B. Chem. Rev. 2016, 116, 9091. doi: 10.1021/acs.chemrev.6b00193 pmid: 22519511
	(d) Sandford, C.; Aggarwal, V. K. Chem. Commun. 2017, 53, 5481. doi: 10.1039/C7CC01254C pmid: 22519511
	(e) Smoum, R.; Rubinstein, A.; Dembitsky, V. M.; Srebnik, M. Chem. Rev. 2012, 112, 4156. doi: 10.1021/cr608202m pmid: 22519511
[2]	(a) Brown, H. C.; Rao, B. C. S. J. Am. Chem. Soc. 1956, 78, 5694. doi: 10.1021/ja01602a063
	(b) Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486.
	(c) Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1977, 99, 5514. doi: 10.1021/ja00458a064
	(d) Masamune, S.; Kim, B. M.; Petersen, J. S.; Sato, T.; Veenstra, S. J. J. Am. Chem. Soc. 1985, 107, 4549. doi: 10.1021/ja00301a032
[3]	(a) Männig, D.; Nöth, H. Angew. Chem., Int. Ed. 1985, 24, 878.
	(b) Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1988, 53, 5178. doi: 10.1021/jo00256a059
	(c) Hayashi, D.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426. doi: 10.1021/ja00191a049
[4]	(a) Collins, B. S. L.; Wilson, C. M.; Myers, E. L.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2017, 56, 11700. doi: 10.1002/anie.201701963
	(b) Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 2003, 4695. doi: 10.1002/ejoc.200300433
	(c) Carrol, A. -M.; O’Sullivan, T. P.; Guiry, P. J. Adv. Synth. Catal. 2005, 347, 609. doi: 10.1002/adsc.200404232
	(d) Chen, J. H.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075. doi: 10.1002/cjoc.201800314
	(e) Guo, J.; Cheng, Z. Y.; Chen, J. H.; Chen, X.; Lu, Z. Acc. Chem. Res. 2021, 54, 11, 2701. doi: 10.1021/acs.accounts.0c00678
	(f) Chen, J. H.; Lu, Z. Org. Chem. Front. 2018, 5, 260. doi: 10.1039/C7QO00613F
[5]	Sato, M.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1990, 31, 231.
[6]	(a) Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc., Chem. Commun. 1993, 1673.
	(b) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. doi: 10.1021/ja00088a047
	(c) Brunel, G. -M.; Buono, G. Tetrahedron Lett. 1999, 40, 3561. doi: 10.1016/S0040-4039(99)00538-9
[7]	Pérez Luna, A.; Ceschi, M. A.; Bonin, M.; Micouin, L.; Husson, H.-P.; Gougeon, S.; Estenne-Bouhtou, G.; Marabout, B.; Sevrin, M.; George, P. J. Org. Chem. 2002, 67, 3522. pmid: 12003572
	(b) Luna, A. P.; Bonin, M.; Micouin, L.; Husson, H.-P. J. Am. Chem. Soc. 2002, 124, 12098. doi: 10.1021/ja026714m pmid: 12003572
	(c) Alexakis, A.; Polet, D.; Bournaud, C.; Bonin, M.; Micouin, L. Tetrahedron: Asymmetry 2005, 16, 3672. pmid: 12003572
[8]	Lee, H.; Lee, B. Y.; Yun, J. Org. Lett. 2015, 17, 764. doi: 10.1021/ol503598w
[9]	(a) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. doi: 10.1021/ja034210y pmid: 29134770
	(b) Edwards, A.; Rubina, M.; Rubin, M. Chem.-Eur. J. 2018, 24, 1394. doi: 10.1002/chem.201704443 pmid: 29134770
[10]	(a) Valk, J. M.; Whitlock, G. A.; Layzell, T. P.; Brown, J. M. Tetrahedron: Asymmetry 1995, 6, 2593.
	(b) Doucet, H.; Fernandez, E.; Layzell, T. P.; Brown, J. M. Chem.- Eur. J. 1999, 5, 1320.
	(c) McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
[11]	Wiesauer, C.; Weissensteiner, W. Tetrahedron: Asymmetry 1996, 7, 5.
[12]	(a) Noh, D.; Chea, H.; Ju, J.; Yun, J. Angew. Chem., Int. Ed. 2009, 48, 6062. doi: 10.1002/anie.200902015 pmid: 30895787
	(b) Xi, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2017, 139, 12758. doi: 10.1021/jacs.7b07124 pmid: 30895787
	(c) Noh, D.; Yoon, S. K.; Won, J.; Lee, J. Y.; Yun, J. Chem.-Asian J. 2011, 6, 1967. doi: 10.1002/asia.201100146 pmid: 30895787
	(d) Jang, W. J.; Song, S. M.; Park, Y.; Yun, J. J. Org. Chem. 2019, 84, 4429. doi: 10.1021/acs.joc.8b03045 pmid: 30895787
[13]	(a) Chen, X.; Cheng, Z.; Lu, Z. ACS Catal. 2019, 9, 4025. doi: 10.1021/acscatal.8b05135 pmid: 30740530
	(b) Chen, X.; Cheng, Z. Y.; Guo, J.; Lu, Z. Nat. Commun. 2018, 9, 3939. doi: 10.1038/s41467-018-06240-y pmid: 30740530
	(c) Chen, C. H.; Wang, H. L.; Li, T. T.; Lu, D. P.; Li, J. J.; Zhang, X.; Hong, X.; Lu, Z. Angew. Chem., Int. Ed. 2022, 61, e202205619. pmid: 30740530
	(d) Obligacion, J. V.; Chirik, P. J. J. Am. Chem. Soc. 2013, 135, 19107. doi: 10.1021/ja4108148 pmid: 30740530
	(e) Palmer, W. N.; Diao, T. N.; Pappas, I.; Chirik, P. J. ACS Catal. 2015, 5, 622. doi: 10.1021/cs501639r pmid: 30740530
	(f) Ogawa, T.; Ruddy, A. J.; Sydora, O. L.; Stradiotto, M.; Turculet, M. Organometallics 2017, 36, 417. doi: 10.1021/acs.organomet.6b00823 pmid: 30740530
	(g) Obligacion, J. V.; Chirik, P. J. Nat. Rev. Chem. 2018, 2, 15. doi: 10.1038/s41570-018-0001-2 pmid: 30740530
[14]	(a) Evans, D. A.; Fu, G. C. J. Am. Chem. Soc. 1991, 113, 4042. doi: 10.1021/ja00010a083
	(b) Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. doi: 10.1021/ja00043a009
[15]	(a) Smith, S. M.; Thacker, N. C.; Takacs, J. M. J. Am. Chem. Soc. 2008, 130, 3734. doi: 10.1021/ja710492q pmid: 31183035
	(b) Smith, S. M.; Uteuliyev, M.; Takacs, J. M. Chem. Commun. 2011, 47, 7812. doi: 10.1039/c1cc11746g pmid: 31183035
	(c) Hoang, G. L.; Yang, Z.-D.; Smith, S. M.; Pal, R.; Miska, J. L.; Pérez, D. E.; Pelter, L. S. W.; Zeng, X. C.; Takacs, J. M. Org. Lett. 2015, 17, 940. doi: 10.1021/ol503764d pmid: 31183035
	(d) Yang, Z. D.; Pal, R.; Hoang, G. L.; Zeng, X. C.; Takacs, J. M. ACS Catal. 2014, 4, 763. doi: 10.1021/cs401023j pmid: 31183035
	(e) Hoang, G. L.; Takacs, J. M. Chem. Sci. 2017, 8, 4511. doi: 10.1039/c7sc01093a pmid: 31183035
	(f) Hoang, G. L.; Zhang, S.; Takacs, J. M. Chem. Commun. 2018, 54, 4838. doi: 10.1039/C8CC01563E pmid: 31183035
	(g) Chakrabarty, S.; Palencia, H.; Morton, M. D.; Carr, R. O.; Takacs, J. M. Chem. Sci. 2019, 10, 4854. doi: 10.1039/c8sc05613g pmid: 31183035
[16]	(a) Smith, S. M.; Takacs, J. M. J. Am. Chem. Soc. 2010, 132, 1740. doi: 10.1021/ja908257x pmid: 31134137
	(b) Shoba, V. M.; Thacker, N. C.; Bochat, A. J.; Takacs, J. M. Angew. Chem., Int. Ed. 2016, 55, 1465. doi: 10.1002/anie.201509137 pmid: 31134137
	(c) Chakrabarty, S.; Takacs, J. M. J. Am. Chem. Soc. 2017, 139, 6066. doi: 10.1021/jacs.7b02324 pmid: 31134137
	(d) Chakrabarty, S.; Takacs, J. M. ACS Catal. 2018, 8, 10530. doi: 10.1021/acscatal.8b03591 pmid: 31134137
[17]	Zhao, W.; Chen, K.-Z.; Li, A.-Z.; Li, B.-J. J. Am. Chem. Soc. 2022. 144, 13071. doi: 10.1021/jacs.2c05993 pmid: 35830595
[18]	Xi, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2016, 138, 6703. doi: 10.1021/jacs.6b02478
[19]	Toure, M.; Chuzel, O.; Parrain, J.-L. J. Am. Chem. Soc. 2012, 134, 17892. doi: 10.1021/ja309018f
[20]	Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed. 2013, 52, 3989. doi: 10.1002/anie.201208610
[21]	Bai, X.-Y.; Zhao, W.; Sun, X.; Li, B.-J. J. Am. Chem. Soc. 2019, 141, 19870. doi: 10.1021/jacs.9b10578
[22]	Dong, W.; Xu, X.; Ma, H.; Lei, Y.; Lin, Z.; Zhao, W. J. Am. Chem. Soc. 2021, 143, 10902. doi: 10.1021/jacs.1c06697
[23]	(a) Jin, S. N.; Liu, K.; Wang, S.; Song, Q. L. J. Am. Chem. Soc. 2021, 143, 13124. doi: 10.1021/jacs.1c04248
	(b) You, Y. E.; Ge, S. Z. Angew. Chem., Int. Ed. 2021, 60, 20684. doi: 10.1002/anie.202107405
	(c) Cheng, Z. Y.; Guo, J.; Sun, Y. F.; Zheng, Y. S.; Zhou, Z. H.; Lu, Z. Angew. Chem., Int. Ed. 2021, 60, 22454. doi: 10.1002/anie.202109089
[24]	(a) Gao, T.-T.; Zhang, W.-W.; Sun, X.; Lu, H.-X.; Li, B.-J. J. Am. Chem. Soc. 2019, 141, 4670. doi: 10.1021/jacs.8b13520
	(b) Gao, T.-T.; Lu, H.-X.; Gao, P.-C.; Li, B.-J. Nat. Commun. 2021, 12, 3776. doi: 10.1038/s41467-021-24012-z