Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones

doi:10.6023/cjoc202109036

Abstract

Phenylselenenic acid and phenylseleninic acid were formed in situ in the reaction of diphenyl diselenide with 1-fluoropyridine trifluoromethane sulfonate (FP-OTf) in air. This mixture can catalyze the conversion of aldoxime to nitrile or ketoxime to ketone, respectively. The catalytic effect on those two kinds of reactions can be improved by changing the amount of diphenyl diselenide and the ratio of diphenyl diselenide to FP-OTf. Nitriles were obtained from the open-air reaction of aldoxime catalyzed by the mixture of diphenyl diselenide (5 mol%) and FP-OTf (4 mol%) with the yields of 57%~94%. In the conversion of ketoximes to ketones, higher yields of ketones (74%~91%) were obtaied when the ratio of diphenyl diselenide to FP-OTf was 1∶1.2 and the dosage of diphenyl diselenide was 2.5 mol%.

Key words: oxime, nitrile, ketone, diphenyl diselenide, 1-fluoropyridine trifluoromethane sulfonate, catalysis

Cite this article

Liming Wang, Ke Li, Wanxuan Zhang. Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1235-1240.

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References 24

[1]	(a) Guo, R.; Liao, L.; Zhao, X. Molecules 2017, 22, 835. doi: 10.3390/molecules22050835
	(b) Ortgies, S.; Breder, A. ACS Catal. 2017, 7, 5828. doi: 10.1021/acscatal.7b01216
	(c) Freudendahl, D. M.; Santoro, S.; Shahzad, S. A.; Santi, C.; Wirth, T. Angew. Chem., Int. Ed. 2009, 48, 8409. doi: 10.1002/anie.200903893
	(d) Santi, C.; Santoro, S.; Battistelli, B. Curr. Org. Chem. 2010, 14, 2442. doi: 10.2174/138527210793358231
	(e) Santoro, S.; Azeredo, J. B.; Nascimento, V.; Sancineto, L.; Braga, A. L.; Santi, C. RSC Adv. 2014, 4, 31521. doi: 10.1039/C4RA04493B
	(f) Xiao, X.; Guan, C.; Xu, J.; Fu, W.; Yu, L. Green Chem. 2021, 23, 4647. doi: 10.1039/D1GC00961C
[2]	(a) Brink, G.-J.; Fernandes, B. C. M.; van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. J. Chem. Soc., Perkin Trans. 1 2001, 224. pmid: 26574922
	(b) Choi, J. K.; Chang, Y. K.; Hong, S. Y. Tetrahedron Lett. 1988, 29, 1967. doi: 10.1016/S0040-4039(00)82091-2 pmid: 26574922
	(c) Roh, K. R.; Kim, K. S.; Kim, Y. H. Tetrahedron Lett. 1991, 32, 793. doi: 10.1016/S0040-4039(00)74888-X pmid: 26574922
	(d) Ichikawa, H.; Usami, Y.; Arimoto, M. Tetrahedron Lett. 2005, 46, 8665. doi: 10.1016/j.tetlet.2005.10.055 pmid: 26574922
	(e) Zhang, X.; Sun, J.; Ding, Y.; Yu, L. Org. Lett. 2015, 17, 5840. doi: 10.1021/acs.orglett.5b03011 pmid: 26574922
	(f) Wang, F.; Yang, C.; Shi, Y.; Lei, Y. Mol. Catal. 2021, 514, 111849. pmid: 26574922
[3]	(a) Jin, W.; Zheng, P.; Wong, W.-T.; Law, G.-L. Adv. Synth. Catal. 2017, 359, 1588. doi: 10.1002/adsc.201601065
	(b) Chuang, H.-Y.; Schupp, M.; Meyrelles, R.; Maryasin, B.; Maulide, N. Angew. Chem., Int. Ed. 2021, 60, 13778. doi: 10.1002/anie.202100801
[4]	Wu, J.-J.; Xu, J.; Zhao, X. Chem.-Eur. J. 2016, 22, 15265. doi: 10.1002/chem.201603975
[5]	(a) Kawamata, Y.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2016, 138, 5206. doi: 10.1021/jacs.6b01462 pmid: 27064419
	(b) Luo, J.; Cao, Q.; Cao, X.; Zhao, X. Nat. Commun. 2018, 9, 527. doi: 10.1038/s41467-018-02955-0 pmid: 27064419
[6]	(a) Tiecco, M.; Testaferr, L.; Santi, C. Eur. J. Org. Chem. 1999, 797.
	(b) Guo, R.; Huang, J.; Huang, H.; Zhao, X. Org. Lett. 2016, 18, 504. doi: 10.1021/acs.orglett.5b03543
[7]	(a) Fragale, G.; Neuburger, M.; Wirth, T. Chem. Commun. 1998, 1867.
	(b) Fujita, K.; Iwaoka, M.; Tomoda, S. Chem. Lett. 1994, 23, 923. doi: 10.1246/cl.1994.923
	(c) Wirth, T.; Häuptli, S.; Leuenberger, M. Tetrahedron: Asymmetry 1998, 9, 547.
	(d) Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Chem.-Eur. J. 2002, 8, 1118. doi: 10.1002/1521-3765(20020301)8:5【-逻辑与-】#x00026;lt;1118::AID-CHEM1118【-逻辑与-】#x00026;gt;3.0.CO;2-2
	(e) Browne, D. M.; Niyomura, O.; Wirth, T. Org. Lett. 2007, 9, 3169. doi: 10.1021/ol071223y
	(f) Alberto, E. E.; Braga, A. L.; Detty, M. R. Tetrahedron 2012, 68, 10476. doi: 10.1016/j.tet.2012.08.004
	(g) Ortgies, S.; Rode, K.; Koszinowski, K.; Kind, J.; Thiele, C. M.; Rehbein, J.; Breder, A. ACS Catal. 2017, 7, 7578. doi: 10.1021/acscatal.7b02729
[8]	(a) Ortgies, S.; Breder, A. Org. Lett. 2015, 17, 2748. doi: 10.1021/acs.orglett.5b01156 pmid: 25997578
	(b) Zhang, X.; Guo, R.; Zhao, X. Org. Chem. Front. 2015, 2, 1334. doi: 10.1039/C5QO00179J pmid: 25997578
[9]	(a) Hori, T.; Sharpless, K. B. J. Org. Chem. 1979, 44, 4204. doi: 10.1021/jo01337a046 pmid: 15575789
	(b) Hori, T.; Sharpless, K. B. J. Org. Chem. 1979, 44, 4208. doi: 10.1021/jo01337a047 pmid: 15575789
	(c) Mellegaard, S. R.; Tunge, J. A. J. Org. Chem. 2004, 69, 8979. pmid: 15575789
	(d) Carrera, I.; Brovetto, M. C.; Seoane, G. A. Tetrahedron Lett. 2006, 47, 7849. doi: 10.1016/j.tetlet.2006.09.024 pmid: 15575789
	(e) Guo, R.; Huang, J.; Zhao, X. ACS Catal. 2018, 8, 926. doi: 10.1021/acscatal.7b03829 pmid: 15575789
	(f) Cresswell, A. J.; Eey, S. T.-C.; Denmark, S. E. Nat. Chem. 2015, 7, 146. doi: 10.1038/nchem.2141 pmid: 15575789
[10]	Yu, L.; Wang, J.; Chen, T.; Ding, K.; Pan, Y. Chin. J. Org. Chem. 2013, 33, 1096. (in Chinese) doi: 10.6023/cjoc2012012049
	( 俞磊, 王俊, 陈天, 丁克鸿, 潘毅, 有机化学, 2013, 33, 1096.) doi: 10.6023/cjoc2012012049
[11]	(a) Liao, L.; Zhang, H.; Zhao, X. ACS Catal. 2018, 8, 6745. doi: 10.1021/acscatal.8b01595
	(b) Wei, W.; Cui, H.; Yue, H.; Yang, D. Green Chem. 2018, 20, 3197. doi: 10.1039/C8GC01245H
	(c) Wang, T.; Jing, X.; Chen, C.; Yu, L. J. Org. Chem. 2017, 82, 9342. doi: 10.1021/acs.joc.7b01245
	(d) Deng, Z.; Wei, J.; Liao, L.; Huang, H.; Zhao, X. Org. Lett. 2015, 17, 1834. doi: 10.1021/acs.orglett.5b00213
[12]	Trenner, J.; Depken, C.; Weber, T.; Breder, A. Angew. Chem., Int. Ed. 2013, 52, 8952. doi: 10.1002/anie.201303662
[13]	Jing, X.; Yuan, D.; Yu, L. Adv. Synth. Catal. 2017, 359, 1194. doi: 10.1002/adsc.201601353
[14]	Selected examples: (a) Zhang, G. F.; Wen, X.; Wang, Y.; Mo, W. M.; Ding, C. R. Prog. Chem. 2012, 24, 361.
	(b) Zheng, Y.; Wu, A.; Ke, Y.; Cao, H.; Yu, L. Chin. Chem. Lett. 2019, 30, 937. doi: 10.1016/j.cclet.2019.01.012
	(c) Wang, F.; Chen, T.; Shi, Y.; Yu, L. Asian J. Org. Chem. 2021, 10, 614. doi: 10.1002/ajoc.202000675
	(d) Deng, X.; Qian, R.; Zhou, H.; Yu, L. Chin. Chem. Lett. 2021, 32, 1029. doi: 10.1016/j.cclet.2020.09.012
	(e) Song, J. H.; Bae, S. M.; Lee, E. J.; Cho, J. H.; Jung, D. I. Asian J. Chem. 2020, 32, 1676. doi: 10.14233/ajchem.2020.22639
[15]	(a) Grirrane, A.; Corma, A.; Garcia, H. J. Catal. 2009, 268, 350. doi: 10.1016/j.jcat.2009.10.005
	(b) Reitsema, R. J. Org. Chem. 1958, 23, 2038. doi: 10.1021/jo01106a636
	(c) Royals, E. E.; Horne, S. E. J. J. Am. Chem. Soc. 1951, 73, 5856. doi: 10.1021/ja01156a119
[16]	Selected examples: (a) Choudhare, T. S.; Wagare, D. S.; Shirsath, S. E.; Netankar, P. D. J. Chem. Sci. 2021, 133, 69. doi: 10.1007/s12039-021-01939-w
	(b) Hart-Davis, J.; Battioni, P.; Boucher, J.-L.; Mansuy, D. J. Am. Chem. Soc. 1998, 120, 12524. doi: 10.1021/ja981805y
	(c) Yang, S. H.; Chang, S. Org. Lett. 2001, 4209.
	(d) Ishihara, K.; Furuya, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983. doi: 10.1002/1521-3773(20020816)41:16【-逻辑与-】#x00026;lt;2983::AID-ANIE2983【-逻辑与-】#x00026;gt;3.0.CO;2-X
	(e) Yamaguchi, K.; Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N. Angew. Chem., Int. Ed. 2007, 46, 3922. doi: 10.1002/anie.200605004
	(f) Rai, A.; Yadav, L. D. S. Eur. J. Org. Chem. 2013, 2013, 1889. doi: 10.1002/ejoc.201300059
	(g) Tambara, K.; Pantos, G. D. Org. Biomol. Chem. 2013, 11, 2466. doi: 10.1039/c3ob27362h
[17]	(a) Yu, L.; Li, H.; Zhang, X.; Ye, J.; Liu, J.; Xu, Q.; Lautens, M. Org. Lett. 2014, 16, 1346. doi: 10.1021/ol500075h
	(b) Chen, C.; Zhang, X.; Cao, H. Wang, F.; Yu, L.; Xu, Q. Adv. Synth. Catal. 2019, 361, 603. doi: 10.1002/adsc.201801163
[18]	(a) Kakroudi, M. A.; Kazemi, F.; Kaboudin, B. J. Mol. Catal. A: Chem. 2014, 392, 112. doi: 10.1016/j.molcata.2014.04.036
	(b) Abedi, S.; Karimi, B.; Kazemi, F.; Bostina, M.; Vali, H. Org. Biomol. Chem. 2013, 11, 416. doi: 10.1039/C2OB26907D
[19]	Belladona, A. L.; Cervo, R.; Alves, D.; Barcellos, T.; Cargnelutti, R.; Schumacher, R. F. Tetrahedron Lett. 2020, 61, 152035. doi: 10.1016/j.tetlet.2020.152035
[20]	Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697. doi: 10.1021/jo00403a016
[21]	Golebiewski, W. M.; Gucma, M. J. Heterocycl. Chem. 2006, 43, 509. doi: 10.1002/jhet.5570430240
[22]	(a) Lamani, M.; Prabhu, K. R. Angew. Chem., Int. Ed. 2010, 49, 6622. doi: 10.1002/anie.201002635
	(b) Mori, N.; Togo, H. Synlett 2005, 1456.
[23]	Leggio, A.; Gallo, S.; Liguori, A. Tetrahedron Lett. 2017, 58, 1512. doi: 10.1016/j.tetlet.2017.03.007
[24]	Liu, J.; Li, H. Chen, K.-X.; Zuo, J.-P.; Guo, Y.-W.; Tang, W.; Li, X.-W. J. Med. Chem. 2018, 61, 11298. doi: 10.1021/acs.jmedchem.8b01430

Entry	Oxime 1/2	Product 3/4	Yield/%
1^a	1a R¹=Ph, R²=H	3a R¹=Ph	94
2^a	1b R¹=4-Et-C₆H₄, R²=H	3b R¹=4-Et-C₆H₄	76
3^a	1c R¹=4-HOC₆H₄, R²=H	3c R¹=4-HOC₆H₄	88
4^a	1d R¹=4-NCC₆H₄, R²=H	3d R¹=4-NCC₆H₄	57
5^a	1e R¹=4-ClC₆H₄, R²=H	3e R¹=4-ClC₆H₄	67
6^a	1f R¹=3-MeC₆H₄, R²=H	3f R¹=3-Me-C₆H₄	75
7^a	1g R¹=PhCH₂CH₂, R²=H	3g R¹=PhCH₂CH₂	84
8^a	1h R¹=4-i-PrC₆H₄CH₂CHCH₃, R²=H	3h R¹=4-i-PrC₆H₄CH₂CHCH₃	80
9^b^,^c	2a R¹=Ph, R²=CH₃	4a R¹=Ph, R²=CH₃	88
10^b^,^c	2bR¹=4-NO₂C₆H₄, R²=CH₃	4b R¹=4-NO₂C₆H₄, R²=CH₃	74
11^b^,^c	2c R¹=4-MeC₆H₄, R²=CH₃	4c R¹=4-MeC₆H₄, R²=CH₃	85
12^b^,^d	2d R¹=4-ClC₆H₄, R²=CH₃	4d R¹=4-ClC₆H₄, R²=CH₃	90
13^b^,^d	2e R¹=4-CH₃OC₆H₄, R²=CH₃	4e R¹=4-CH₃OC₆H₄, R²=CH₃	75
14^b^,^e	2f R¹=Ph, R²=Ph	4f R¹=Ph, R²=Ph	91
15^b^,^d	2g	4g	78

Entry	Oxime 1/2	Product 3/4	Yield/%
1^a	1a R¹=Ph, R²=H	3a R¹=Ph	94
2^a	1b R¹=4-Et-C₆H₄, R²=H	3b R¹=4-Et-C₆H₄	76
3^a	1c R¹=4-HOC₆H₄, R²=H	3c R¹=4-HOC₆H₄	88
4^a	1d R¹=4-NCC₆H₄, R²=H	3d R¹=4-NCC₆H₄	57
5^a	1e R¹=4-ClC₆H₄, R²=H	3e R¹=4-ClC₆H₄	67
6^a	1f R¹=3-MeC₆H₄, R²=H	3f R¹=3-Me-C₆H₄	75
7^a	1g R¹=PhCH₂CH₂, R²=H	3g R¹=PhCH₂CH₂	84
8^a	1h R¹=4-i-PrC₆H₄CH₂CHCH₃, R²=H	3h R¹=4-i-PrC₆H₄CH₂CHCH₃	80
9^b^,^c	2a R¹=Ph, R²=CH₃	4a R¹=Ph, R²=CH₃	88
10^b^,^c	2bR¹=4-NO₂C₆H₄, R²=CH₃	4b R¹=4-NO₂C₆H₄, R²=CH₃	74
11^b^,^c	2c R¹=4-MeC₆H₄, R²=CH₃	4c R¹=4-MeC₆H₄, R²=CH₃	85
12^b^,^d	2d R¹=4-ClC₆H₄, R²=CH₃	4d R¹=4-ClC₆H₄, R²=CH₃	90
13^b^,^d	2e R¹=4-CH₃OC₆H₄, R²=CH₃	4e R¹=4-CH₃OC₆H₄, R²=CH₃	75
14^b^,^e	2f R¹=Ph, R²=Ph	4f R¹=Ph, R²=Ph	91
15^b^,^d	2g	4g	78

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