环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应

doi:10.6023/cjoc202205031

摘要/Abstract

报道了利用环状三价碘试剂进行底物极性反转, 一锅法获得β-二羰基类底物α-苯甲酰氧基化产物的新方法. 反应成功的关键在于体系中原位生成了烯醇硅醚结构单元, 最终经过电性诱导极性反转中间体的氧化还原重排而完成转化. 该反应具有良好的原子经济性, 不仅适合克级规模制备和后续衍生化应用, 而且拓展了环状三价碘及其衍生物在极性反转领域的应用范围.

关键词: 三价碘试剂, β-二羰基化合物, α-苯甲酰氧基化, 极性反转

A one-pot method for the α-benzoyloxylation of β-dicarbonyl compounds using trivalent iodine reagent was developed. The success of this protocol hinges on the the in situ generation of silylenol ether structure followed by electrical property-promoted reductive rearrangement of a umpolung intermediate. This reaction has good atomic economy, which is not only suitable for gram scale preparation and subsequent derivatization applications, but also expands the application range of cyclic trivalent iodine and its derivatives in the field of polarity reversal.

Key words: trivalent iodine reagent, β-dicarbonyl compound, α-benzoyloxylation, umpolung

引用此文

高珠鹏, 项锴, 徐学涛, 张雅婷, 朱道勇. 环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应[J]. 有机化学, 2022, 42(11): 3766-3775.

Zhupeng Gao, Kai Xiang, Xuetao Xu, Yating Zhang, Daoyong Zhu. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3766-3775.

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[1]	Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. pmid: 12105935
[2]	Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. doi: 10.1021/cr800332c pmid: 18986207
[3]	Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. doi: 10.1021/acs.chemrev.5b00547 pmid: 26861673
[4]	Koposov, A. Y.; Netzel, B. C.; Yusubov, M. S.; Nemykin, V. N.; Nazarenko, A. Y.; Zhdankin, V. V. Eur. J. Org. Chem. 2007, 2007, 4475. doi: 10.1002/ejoc.200700625
[5]	Yusubov, M. S.; Yusubova, R. Y.; Funk, T. V.; Chi, K.-W.; Zhdankin, V. V. Synthesis 2009, 2009, 2505. doi: 10.1055/s-0029-1216870
[6]	Miyamoto, K.; Yokota, Y.; Suefuji, T.; Yamaguchi, K.; Ozawa, T.; Ochiai, M. Chem.-Eur. J. 2014, 20, 5447. doi: 10.1002/chem.201304961
[7]	Chen, H.; Wang, L.; Han, J. Org. Lett. 2020, 22, 3581. doi: 10.1021/acs.orglett.0c01024
[8]	Chen, H.; Han, J.; Wang, L. Angew. Chem., Int. Ed. 2018, 57, 12313. doi: 10.1002/anie.201806405
[9]	Linde, E.; Bulfield, D.; Kervefors, G.; Purkait, N.; Olofsson, B. Chem 2022, 8, 850. doi: 10.1016/j.chempr.2022.01.009
[10]	Greaney, M. F.; Motherwell, W. B. Tetrahedron Lett. 2000, 41, 4463.
[11]	Ochiai, M.; Miyamoto, K. Eur. J. Org. Chem. 2008, 2008, 4229. doi: 10.1002/ejoc.200800416
[12]	Seebach, D. Angew. Chem., nt. Ed. 1979, 18, 239.
[13]	Baragwanath, L.; Rose, C. A.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2009, 74, 9214. doi: 10.1021/jo902018j pmid: 19950884
[14]	Desvergnes, S.; Py, S.; Vallée, Y. J. Org. Chem. 2005, 70, 1459. pmid: 15704985
[15]	Exner, C. J.; Laclef, S.; Poli, F.; Turks, M.; Vogel, P. J. Org. Chem. 2011, 76, 840. doi: 10.1021/jo102035d
[16]	Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., nt. Ed. 2012, 51, 11686.
[17]	De Joarder, D.; Jennings, M. P. Eur. J. Org. Chem. 2015, 2015, 3303. doi: 10.1002/ejoc.201500287
[18]	Canesi, S. Synlett 2019, 30, 647. doi: 10.1055/s-0037-1610340
[19]	Xi, Y.-K.; Zhang, H.; Li, R.-X.; Kang, S.-Y.; Li, J.; Li, Y. Chem.-Eur. J. 2019, 25, 3005. doi: 10.1002/chem.201806411
[20]	Eisenberger, P.; Gischig, S.; Togni, A. Chem.-Eur. J. 2006, 12, 2579. pmid: 16402401
[21]	Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342. doi: 10.1021/ol2005903
[22]	Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202. doi: 10.1021/ja504458j pmid: 24983408
[23]	Ge, J.; Ding, Q.; Wang, X.; Peng, Y. J. Org. Chem. 2020, 85, 7658. doi: 10.1021/acs.joc.9b03470
[24]	Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., nt. Ed. 2009, 48, 9346.
[25]	Fernández González, D.; Brand, J. P.; Waser, J. Chem.-Eur. J. 2010, 16, 9457. doi: 10.1002/chem.201001539 pmid: 20645361
[26]	Frei, R.; Waser, J. J. Am. Chem. Soc. 2013, 135, 9620. doi: 10.1021/ja4044196
[27]	Chen, C. C.; Waser, J. Chem. Commun. 2014, 50, 12923. doi: 10.1039/C4CC06851C
[28]	Chen, C. C.; Waser, J. Org. Lett. 2015, 17, 736. doi: 10.1021/acs.orglett.5b00015
[29]	Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192. doi: 10.1021/ja954119x
[30]	Deng, Q.-H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356. doi: 10.1021/ja402082p
[31]	Zhang, B.; Studer, A. Org. Lett. 2013, 15, 4548. doi: 10.1021/ol402106x pmid: 23930944
[32]	Vita, M. V.; Waser, J. Org. Lett. 2013, 15, 3246. doi: 10.1021/ol401229v
[33]	Vita, M. V.; Caramenti, P.; Waser, J. Org. Lett. 2015, 17, 5832. doi: 10.1021/acs.orglett.5b03002
[34]	Frei, R.; Courant, T.; Wodrich, M. D.; Waser, J. Chem.-Eur. J. 2015, 21, 2662. doi: 10.1002/chem.201406171
[35]	Le Vaillant, F.; Wodrich, M. D.; Waser, J. Chem. Sci. 2017, 8, 1790. doi: 10.1039/c6sc04907a pmid: 28451301
[36]	Egami, H.; Shimizu, R.; Sodeoka, M. Tetrahedron Lett. 2012, 53, 5503. doi: 10.1016/j.tetlet.2012.07.134
[37]	Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882. doi: 10.1021/ol3011419 pmid: 22612441
[38]	Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem.,Int. Ed. 2013, 52, 7841. doi: 10.1002/anie.201303350
[39]	Hari, D. P.; Waser, J. J. Am. Chem. Soc. 2016, 138, 2190. doi: 10.1021/jacs.6b00278
[40]	Bertho, S.; Rey-Rodriguez, R.; Colas, C.; Retailleau, P.; Gillaizeau, I. Chem.-Eur. J. 2017, 23, 17674. doi: 10.1002/chem.201704499
[41]	Wu, D.; Cui, S.-S.; Lin, Y.; Li, L.; Yu, W. J. Org. Chem. 2019, 84, 10978. doi: 10.1021/acs.joc.9b01569
[42]	Banerjee, S.; Senthilkumar, B.; Patil, N. T. Org. Lett. 2019, 21, 180. doi: 10.1021/acs.orglett.8b03651
[43]	Amos, S. G. E.; Nicolai, S.; Waser, J. Chem. Sci. 2020, 11, 11274. doi: 10.1039/D0SC03655B
[44]	Jia, Z.; Gálvez, E.; Sebastián, R. M.; Pleixats, R.; Álvarez-Larena, Á.; Martin, E.; Vallribera, A.; Shafir, A. Angew. Chem., nt. Ed. 2014, 53, 11298.
[45]	Wu, Y.; Arenas, I.; Broomfield, L. M.; Martin, E.; Shafir, A. Chem.-Eur. J. 2015, 21, 18779. doi: 10.1002/chem.201503987
[46]	Tian, J.; Luo, F.; Zhang, C.; Huang, X.; Zhang, Y.; Zhang, L.; Kong, L.; Hu, X.; Wang, Z.-X.; Peng, B. Angew. Chem., nt. Ed. 2018, 57, 9078.
[47]	Zhao, W.; Huang, X.; Zhan, Y.; Zhang, Q.; Li, D.; Zhang, Y.; Kong, L.; Peng, B. Angew. Chem., nt. Ed. 2019, 58, 17210.
[48]	Sousa e Silva, F. C.; Van, N. T.; Wengryniuk, S. E. J. Am. Chem. Soc. 2020, 142, 64. doi: 10.1021/jacs.9b11282
[49]	Tian, J.; Luo, F.; Zhang, Q.; Liang, Y.; Li, D.; Zhan, Y.; Kong, L.; Wang, Z.-X.; Peng, B. J. Am. Chem. Soc. 2020, 142, 6884. doi: 10.1021/jacs.0c00783
[50]	Bhujanga Rao, C.; Yuan, J.; Zhang, Q.; Zhang, R.; Zhang, N.; Fang, J.; Dong, D. J. Org. Chem. 2018, 83, 2904. doi: 10.1021/acs.joc.8b00114
[51]	Yu, J.; Tian, J.; Zhang, C. Adv. Synth. Catal. 2010, 352, 531. doi: 10.1002/adsc.200900737
[52]	Liu, W.-B.; Chen, C.; Zhang, Q.; Zhu, Z.-B. Beilstein J. Org. Chem. 2011, 7, 1436. doi: 10.3762/bjoc.7.167
[53]	Lee, J.; Oya, S.; Snyder, J. K. Tetrahedron Lett. 1991, 32, 5899. doi: 10.1016/S0040-4039(00)79421-4
[54]	Wang, D.; Xu, C.; Zhang, L.; Luo, S. Org. Lett. 2015, 17, 576. doi: 10.1021/ol503592n
[55]	Lloris, M. E.; Gálvez, N.; Marquet, J.; Moreno-Mañas, M. Tetrahedron 1991, 47, 8031. doi: 10.1016/S0040-4020(01)81955-4
[56]	Terent’ev, A. O.; Vil’, V. A.; Nikishin, G. I.; Adam, W. Synlett 2015, 26, 802. doi: 10.1055/s-0034-1379982
[57]	Terent'ev, A. O.; Vil', V. A.; Gorlov, E. S.; Nikishin, G. I.; Pivnitsky, K. K.; Adam, W. J. Org. Chem. 2016, 81, 810. doi: 10.1021/acs.joc.5b02233
[58]	Bityukov, O. V.; Matveeva, O. K.; Vil', V. A.; Kokorekin, V. A.; Nikishin, G. I.; Terent'ev, A. O. J. Org. Chem. 2019, 84, 1448. doi: 10.1021/acs.joc.8b02791 pmid: 30618255
[59]	Zhang, C.; Chen, X.-M.; Luo, Y.; Li, J.-L.; Chen, M.; Hai, L.; Wu, Y. ACS Sustainable Chem. Eng. 2018, 6, 13473. doi: 10.1021/acssuschemeng.8b03399
[60]	Dar'in, D.; Kantin, G.; Krasavin, M. Chem. Commun. 2019, 55, 5239. doi: 10.1039/C9CC02042J
[61]	Wang, X.; Ding, Y.; Tao, Y.; Wang, Z.; Wang, Z.; Yan, J. Polym. Chem. 2020, 11, 1708. doi: 10.1039/D0PY00185F
[62]	Zhu, J.; Germain, A. R.; Porco Jr, J. A. Angew. Chem.,Int. Ed. 2004, 43, 1239. doi: 10.1002/anie.200353037
[63]	Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., nt. Ed. 2011, 50, 5331.
[64]	Reddi, R. N.; Prasad, P. K.; Sudalai, A. Org. Lett. 2014, 16, 5674. doi: 10.1021/ol5027393
[65]	Mao, J.; Liu, D.; Li, Y.; Zhao, J.; Rong, G.; Yan, H.; Zhang, G. Catal. Commun. 2015, 70, 62. doi: 10.1016/j.catcom.2015.07.013
[66]	Chang, L.-M.; Yuan, G.-Q. Tetrahedron 2016, 72, 7003. doi: 10.1016/j.tet.2016.09.031
[67]	Li, C.; Jin, T.; Zhang, X.; Li, C.; Jia, X.; Li, J. Org. Lett. 2016, 18, 1916. doi: 10.1021/acs.orglett.6b00749
[68]	Li, J.; Yang, Z.; Yang, T.; Yi, J.; Zhou, C. New J. Chem. 2018, 42, 1581. doi: 10.1039/C7NJ03989A
[69]	Mizar, P.; Wirth, T. Angew. Chem.,Int. Ed. 2014, 53, 5993. doi: 10.1002/anie.201400405
[70]	Iinuma, M.; Moriyama, K.; Togo, H. Eur. J. Org. Chem. 2014, 2014, 772. doi: 10.1002/ejoc.201301466
[71]	Harper, M. J.; Emmett, E. J.; Bower, J. F.; Russell, C. A. J. Am. Chem. Soc. 2017, 139, 12386. doi: 10.1021/jacs.7b06668
[72]	Revol-Cavalier, J.; Bultel-Poncé, V.; Guy, A.; Durand, T.; Oger, C.; Galano, J.-M. Org. Lett. 2020, 22, 7455. doi: 10.1021/acs.orglett.0c02553 pmid: 32937076

Entry	Solvent	Temperature	Et₃N (equiv.)	3aa^b/%
1	CH₂Cl₂	－78 ℃ to r.t.	1.3	n.d.^c^,^d
2	CH₂Cl₂	－78 ℃ to r.t.	1.3	60
3	CH₂Cl₂	－78 ℃ to r.t.	1.5	40
4	CH₂Cl₂	－78 ℃ to r.t.	1.7	30
5	CH₂Cl₂	－78 ℃ to r.t.	2.1	30
6	CH₂Cl₂	－78 ℃ to r.t.	2.3	20
7	THF	－78 ℃ to r.t.	1.3	Trace
8	Cyclohexane	－78 ℃ to r.t.	1.3	57
9	n-Heptane	－78 ℃ to r.t.	1.3	61
10	toluene	－78 ℃ to r.t.	1.3	60
11	n-Hexane	－78 ℃ to r.t.	1.3	67
12	n-Hexane	－78 ℃ to r.t.	1.0	29
13	n-Hexane	－78 ℃ to r.t.	1.1	34
14	n-Hexane	－78 ℃ to r.t.	1.5	52
15	n-Hexane	－78 ℃ to r.t.	1.7	56
16	n-Hexane	－78 ℃ to r.t.	2.0	69
17	n-Hexane	－78 ℃ to r.t.	2.2	24
18	n-Hexane	－60 ℃ to r.t.	2.0	66
19	n-Hexane	－40 ℃ to r.t.	2.0	73
20	n-Hexane	－20 ℃ to r.t.	2.0	64
21	n-Hexane	0 ℃ to r.t.	2.0	52
22	n-Hexane	60 ℃	2.0	70
23	n-Hexane	70 ℃	2.0	61

Entry	Solvent	Temperature	Et₃N (equiv.)	3aa^b/%
1	CH₂Cl₂	－78 ℃ to r.t.	1.3	n.d.^c^,^d
2	CH₂Cl₂	－78 ℃ to r.t.	1.3	60
3	CH₂Cl₂	－78 ℃ to r.t.	1.5	40
4	CH₂Cl₂	－78 ℃ to r.t.	1.7	30
5	CH₂Cl₂	－78 ℃ to r.t.	2.1	30
6	CH₂Cl₂	－78 ℃ to r.t.	2.3	20
7	THF	－78 ℃ to r.t.	1.3	Trace
8	Cyclohexane	－78 ℃ to r.t.	1.3	57
9	n-Heptane	－78 ℃ to r.t.	1.3	61
10	toluene	－78 ℃ to r.t.	1.3	60
11	n-Hexane	－78 ℃ to r.t.	1.3	67
12	n-Hexane	－78 ℃ to r.t.	1.0	29
13	n-Hexane	－78 ℃ to r.t.	1.1	34
14	n-Hexane	－78 ℃ to r.t.	1.5	52
15	n-Hexane	－78 ℃ to r.t.	1.7	56
16	n-Hexane	－78 ℃ to r.t.	2.0	69
17	n-Hexane	－78 ℃ to r.t.	2.2	24
18	n-Hexane	－60 ℃ to r.t.	2.0	66
19	n-Hexane	－40 ℃ to r.t.	2.0	73
20	n-Hexane	－20 ℃ to r.t.	2.0	64
21	n-Hexane	0 ℃ to r.t.	2.0	52
22	n-Hexane	60 ℃	2.0	70
23	n-Hexane	70 ℃	2.0	61