t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

doi:10.6023/cjoc202102025

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3144-3156.DOI: 10.6023/cjoc202102025 Previous Articles Next Articles

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t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用

孙佳兵^a, 苗涛^a^,^*(), 李品华^a, 王磊^a^,^b^,^c^,^*()

a 淮北师范大学化学与材料科学学院绿色和精准合成化学及应用教育部重点实验室安徽淮北 235000
b 台州学院医药化工与材料工程学院浙江台州 318000
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2021-02-09 修回日期:2021-05-07 发布日期:2021-05-25
通讯作者: 苗涛, 王磊
基金资助:
国家自然科学基金(21772062); 国家自然科学基金(22071171); 国家自然科学基金(21602072); 安徽省高校自然科学基金(KJ2019ZD66)

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

Jiabing Sun^a, Tao Miao^a(), Pinhua Li^a, Lei Wang^a^,^b^,^c()

a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huabei, Anhui 235000
b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2021-02-09 Revised:2021-05-07 Published:2021-05-25
Contact: Tao Miao, Lei Wang
Supported by:
National Natural Science Foundation of China(21772062); National Natural Science Foundation of China(22071171); National Natural Science Foundation of China(21602072); Anhui University Natural Science Research Project(KJ2019ZD66)

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Abstract

A t-BuOK-mediated desulfonylation/dehydrogenation cascade reaction of (Z)-C6-(vinyl sulfone)phenanthridines is described. This process provides a novel and efficient strategy for the synthesis of 1,3-dienes with phenanthridinyl units in good yields under transition-metal-free conditions. Furthermore, the application of the generated 1,3-dienes in the [4+2] cycloaddition has been demonstrated by reacting with dienophiles such as fumaronitrile in a two-step procedure.

Key words: t-BuOK, desulfonylation, 1,3-conjugated dienes, cycloaddition reactions

Cite this article

Jiabing Sun, Tao Miao, Pinhua Li, Lei Wang. t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3144-3156.

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Fig. & Tab. 7

References 20

[1]	(a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds, Academic, New York, 1972, Vol. II. pmid: 17221987
	(b) Pereira, A. R.; Cabezas, J. A. J. Org. Chem. 2005, 70, 2594. pmid: 17221987
	(c) Figueiredo, R. M.; Berner, R.; Julis, J.; Liu, T.; Turp, D.; Christmann, M. J. Org. Chem. 2007, 72, 640. pmid: 17221987
	(d) Nicolaou, K. C.; Daines, R. A.; Ogawa, Y.; Chakraborty, T. K. J. Am. Soc. Chem. 1988, 110, 4696. doi: 10.1021/ja00222a030 pmid: 17221987
	(e) Negishi, E.-I.; Wang, G. In Science of Synthesis, Eds.: Jacobsen, E. N.; Meijere, A., Thieme, Stuttgart, 2010, Vol. 47, p. 909. pmid: 17221987
[2]	(a) Rappoport, Z. The Chemistry of Dienes and Polyenes, John Wiley & Sons, Chichester, 1997, Vol. 1; 2001, Vol. 2.
	(b) Nicolaou, K. C.; Snyder, S. S.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., nt. Ed. 2002, 41, 1668.
	(c) Negishi, E.-I.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474. doi: 10.1021/ar800038e
[3]	(a) Metzker, M. L.; Lu, J.; Gibbs, R. A. Science 1996, 271, 1420. pmid: 8596915
	(b) Valente, A.; Mortreux, A.; Visseaux, M.; Zinck, P. Chem. Rev. 2013, 113, 3836. doi: 10.1021/cr300289z pmid: 8596915
[4]	(a) Normant, J. F. Modern Synthetic Methods, Ed.: Scheffold, R., Wiley, Chichester, 1983; Vol. 3, p. 139.
	(b) Larock, R. C. Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989, p. 241.
	(c) Sellén, M.; Bäckvall, J.-E.; Helquist, P. J. Org. Chem., 1991, 56, 835. doi: 10.1021/jo00002a061
[5]	(a) Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 87, 1318. doi: 10.1002/(ISSN)1099-0682 pmid: 21648453
	(b) Dong, D. J.; Li, H. H.; Tian, S. K. J. Am. Soc. Chem. 2010, 132, 5018. doi: 10.1021/ja910238f pmid: 21648453
	(c) Hampton, C. S.; Harmata, M. Org. Lett. 2014, 16, 1256. doi: 10.1021/ol500259m pmid: 21648453
	(d) Jacobsen, M. J.; Funder, E. D.; Cramer, J. R.; Gothelf, K. V. Org. Lett. 2011, 13, 3418. doi: 10.1021/ol2011677 pmid: 21648453
	(e) Xu, S.; Zhou, L.; Zeng, S.; Ma, R.; Wang, Z.; He, Z. Org. Lett. 2009, 11, 3498. doi: 10.1021/ol901334c pmid: 21648453
[6]	(a) Horner, L.; Hoffmann, H.; Wippel, H. G.; Klahre, G. Chem. Ber. 1959, 92, 2499. doi: 10.1002/(ISSN)1099-0682
	(b) Wadsworth, W. S.; Emmons, W. D., Jr., J. Am. Soc. Chem. 1961, 83, 1733. doi: 10.1021/ja01468a042
	(c) Wadsworth, W. S. Org. React. 1977, 25, 73.
[7]	(a) Julia, M.; Paris, J. M. Tetrahedron Lett. 1973, 14, 4833. doi: 10.1016/S0040-4039(01)87348-2
	(b) Blakemore, P. R. J. J. Chem. Soc., erkin Trans. 1 2002, 2563.
	(c) Aïssa, C. Eur. J. Org. Chem. 2009, 1831.
	(d) Markó, I. E.; Pospíšil, J. In Science of Synthesis, Vol.47a, Eds.: Alkenes; de Meijere, A., George Thieme Verlag, Stuttgart, 2009, 105.
[8]	Peterson, D. J. J. Org. Chem. 1968, 33, 780. doi: 10.1021/jo01266a061
[9]	(a) Wojtkielewicz, A. Curr. Org. Synth. 2013, 10, 43. doi: 10.2174/157017913804810942 pmid: 29936839
	(b) Cornil, J.; Echeverria, P.-G.; Phansavath, P.; Ratovelomanana- Vidal, V.; Guérinot, A.; Cossy, J. Org. Lett. 2015, 17, 948. doi: 10.1021/acs.orglett.5b00042 pmid: 29936839
	(c) Stille, J. K. Angew. Chem., nt. Ed. 1986, 25, 508. pmid: 29936839
	(d) Heck, R. F. Org. React. 1982, 27, 345. pmid: 29936839
	(e) Yoon, C. H.; Yoo, K. S.; Yi, S. W.; Mishra, R. K.; Jung, K. W. Org. Lett. 2004, 6, 4037. doi: 10.1021/ol0483192 pmid: 29936839
	(f) Molander, G. A.; Yokoyama, Y. J. Org. Chem. 2006, 71, 2493. pmid: 29936839
	(g) Nguyen, V. T.; Dang, H. T.; Pham, H. H.; Nguyen, V. D.; Flores-Hansen, C.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2018, 140, 8434. doi: 10.1021/jacs.8b05421 pmid: 29936839
	(h) Fiorito, D.; Folliet, S.; Liu, Y.; Mazet, C. ACS Catal. 2018, 8, 1392. doi: 10.1021/acscatal.7b04030 pmid: 29936839
	(i) He, R.; Deng, M.-Z. Org. Lett. 2002, 4, 2759. doi: 10.1021/ol026286p pmid: 29936839
[10]	(a) Xu, Y.-H.; Lu, J.; Loh, T.-P. J. Am. Soc. Chem. 2009, 131, 1372. doi: 10.1021/ja8084548
	(b) Xu, Y.-H.; Chok, Y. K.; Loh, T.-P. Chem. Sci. 2011, 2, 1822. doi: 10.1039/c1sc00262g
[11]	Yu, H.; Jin, W.; Sun, C.; Chen, J.; Du, W.; He, S.; Yu, Z. Angew. Chem., nt. Ed. 2010, 49, 5792.
[12]	(a) Hatamoto, Y.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2004, 6, 4623. pmid: 15548091
	(b) Besset, T.; Kuhl, N.; Patureau, F. W.; Glorius, F. Chem.-Eur. J. 2011, 17, 7167. doi: 10.1002/chem.v17.26 pmid: 15548091
	(c) Zhang, Y.; Cui, Z.; Li, Z.; Liu, Z.-Q. Org. Lett. 2012, 14, 1838. doi: 10.1021/ol300442w pmid: 15548091
	(d) Meng, K.; Sun, Y.; Zhang, J.; Zhang, K.; Ji, X.; Ding, L.; Zhong, G. Org. Lett. 2019, 21, 8219. doi: 10.1021/acs.orglett.9b02935 pmid: 15548091
	(e) Gong, T.-J.; Su, W.; Liu, Z.-J.; Cheng, W.-M.; Xiao, B.; Fu, Y. Org. Lett. 2014, 16, 330. doi: 10.1021/ol403407q pmid: 15548091
[13]	(a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. pmid: 19572654
	(b) Mori, M. Ene-Yne Metathesis. In Handbook of Metathesis, Ed.: Grubbs, R. H., Wiley-VCH, Weinheim, Germany, 2003; Vol. 2, p. 176. pmid: 19572654
	(c) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317. doi: 10.1021/cr020009e pmid: 19572654
	(d) Diver, S. T. Sci. Synth. 2009, 46, 97. pmid: 19572654
	(e) Clark, J. R.; Diver, S. T. Org. Lett. 2011, 13, 2896. doi: 10.1021/ol200914j pmid: 19572654
	(f) Alcaide, B.; Almendros, P.; Luna, A. Chem. Rev. 2009, 109, 3817. doi: 10.1021/cr9001512 pmid: 19572654
	(g) Clark, J. R.; Griffiths, J. R.; Diver, S. T. J. Am. Chem. Soc. 2013, 135, 3327. doi: 10.1021/ja4011207 pmid: 19572654
[14]	(a) Nakata, T. Chem. Soc. Rev. 2010, 39, 1955. doi: 10.1039/b902737h pmid: 19438205
	(b) Pathak, T. Tetrahedron 2008, 64, 3605. doi: 10.1016/j.tet.2008.01.069 pmid: 19438205
	(c) Back, T. G.; Clary, K. N.; Gao, D. Chem. Rev. 2010, 110, 4498. doi: 10.1021/cr1000546 pmid: 19438205
	(d) Báckvall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291. doi: 10.1021/cr970326z pmid: 19438205
	(e) Alba, A. R.; Companyo, X.; Rios, R. Chem. Soc. Rev. 2010, 39, 2018. doi: 10.1039/b911852g pmid: 19438205
	(f) Caturla, F.; Náijera, C. Tetrahedron 1998, 54, 11255. doi: 10.1016/S0040-4020(98)00658-9 pmid: 19438205
	(g) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701. pmid: 19438205
	(h) El-Awa, A.; Noshi, M. N.; Jourdin, X. M.; Fuchs, P. L. Chem. Rev. 2009, 109, 2315. doi: 10.1021/cr800309r pmid: 19438205
	(i) Legarda, P.; García-Rubia, D. A.; Gómez Arrayás, R.; Carretero, J. C. Adv. Synth. Catal. 2016, 358, 1065. doi: 10.1002/adsc.201501129 pmid: 19438205
	(j) Tang, Y.; Ran, S.; Wang, P.; Chen, P. Chin. J. Org. Chem. 2019, 39, 1116. (in Chinese) doi: 10.6023/cjoc201810002 pmid: 19438205
	(唐裕才, 冉书童, 王萍, 陈飘, 有机化学, 2019, 39, 1116.) doi: 10.6023/cjoc201810002 pmid: 19438205
	(k) Chen, D.; Sun, Y.; Dong, D.; Han, Q.; Wang, Z. Chin. J. Org. Chem. 2020, 40, 4267. (in Chinese) doi: 10.6023/cjoc202006025 pmid: 19438205
	(陈德茂, 孙媛媛, 董道青, 韩晴晴, 王祖利, 有机化学, 2020, 40, 4267.) doi: 10.6023/cjoc202006025 pmid: 19438205
[15]	(a) Qiao, B.; Liu, Q.; Liu, H.; Yan, L.; Jiang, Z. Chem.-Asian J. 2014, 9, 1252.
	(b) Zhu, Q.; Lu, Y. Org. Lett. 2008, 10, 4803. doi: 10.1021/ol8019296
	(c) Landa, A.; Maestro, M.; Masdeu, C.; Puente, Á.; Vera, S.; Oiarbide, M.; Palomo, C. Chem.-Eur. J. 2009, 15, 1562. doi: 10.1002/chem.v15:7
	(d) Dou, X.; Lu, Y. Org. Biomol. Chem. 2013, 11, 5217. doi: 10.1039/c3ob41267a
	(e) Chepyshev, S. V.; Lujan-Montelongo, J. A.; Chao, A.; Fleming, F. F. Angew. Chem., nt. Ed. 2017, 56, 4310.
	(f) Bos, P. H.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2008, 10, 4219. doi: 10.1021/ol801566n
[16]	(a) Náijera, C.; Yus, M. Tetrahedron 1999, 55, 10547. doi: 10.1016/S0040-4020(99)00600-6
	(b) Braun, M.-G.; Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 2011, 133, 15954. doi: 10.1021/ja207944c
	(c) Chang, M.; Wu, Y.; Tsai, Y.; Chen, H. J. Org. Chem. 2019, 84, 11699. doi: 10.1021/acs.joc.9b01606
[17]	(a) Ma, S.; Ren, H.; Wei, Q. J. Am. Chem. Soc. 2003, 125, 4817. doi: 10.1021/ja034039q
	(b) Chen, G.; Yu, Y.; Cai, M. Synth. Commun. 2009, 39, 1478. doi: 10.1080/00397910802531971
	(c) Clayden, J.; Julia, M. J. Chem. Soc., hem. Commun. 1993, 1682.
	(d) Fabre, J. L.; Julia, M.; Verpeaux, J. N. Tetrahedron Lett. 1982, 23, 2469.
	(e) Alvarez, E.; Cuvigny, T.; Hervé du Penhoat, C.; Julia, M. Tetrahedron, 1988, 44, 111. doi: 10.1016/S0040-4020(01)85098-5
	(f) Alvarez, E.; Cuvigny, T.; du Penhoat, C. H.; Julia, M. Tetrahedron 1988, 44, 119. doi: 10.1016/S0040-4020(01)85099-7
	(g) Fukuda, J.; Nogi, K.; Yorimitsu, H. Asian J. Org. Chem. 2018, 7, 2049. doi: 10.1002/ajoc.v7.10
[18]	(a) Theobald, R. S.; Schofield, K. Chem. Rev. 1950, 46, 170. doi: 10.1021/cr60143a004 pmid: 15270564
	(b) Simeon, S.; Rios, J. L.; Villar, A. Pharmazie 1989, 44, 593. pmid: 15270564
	(c) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686. pmid: 15270564
	(d) Nakanishi, T.; Suzuki, M.; Saimoto, A.; Kabasawa, T. J. Nat. Prod. 1999, 62, 864. pmid: 15270564
	(e) Abdel-Halim, O. B.; Morikawa, T.; Ando, S.; Matsuda, H.; Yoshikawa, M. J. Nat. Prod. 2004, 67, 1119. pmid: 15270564
[19]	(a) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., nt. Ed. 2002, 41, 1668.
	(b) Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926. doi: 10.1039/C8CS00274F
	(c) Ju, C.; Wu, Z.; Li, Y.; Zhang, W. Chin. J. Org. Chem. 2020, 40, 3925. (in Chinese) doi: 10.6023/cjoc202004025
	(居辰阳, 吴正兴, 李云艺, 张万斌, 有机化学, 2020, 40, 3925.) doi: 10.6023/cjoc202004025
	(d) Sun, M.; Zhang, J.; Zhang, Y.; Li, P.; Wang, L. Chin. J. Org. Chem. 2020, 40, 2419. (in Chinese) doi: 10.6023/cjoc202003038
	(孙明利, 张家俊, 张义成, 李品华, 王磊, 有机化学, 2020, 40, 2419.) doi: 10.6023/cjoc202003038
[20]	Li, Y.; Miao, T.; Li, P.; Wang, L. Org. Lett. 2018, 20, 1735. doi: 10.1021/acs.orglett.8b00171

Entry	Base	Solvent	Yield^b/%
1	t-BuOK	CH₂Cl₂	40
2	t-BuOK	THF	87
3	t-BuOK	1,4-Dioxane	58
4	t-BuOK	CH₃CN	41
5	t-BuOK	Toluene	17
6	t-BuOK	DMF	30
7	t-BuOK	Acetone	41
8	t-BuOK	DMSO	0
9	t-BuOK	DCE	0
10	t-BuONa	THF	36
11	K₂CO₃	THF	0
12	Na₂CO₃	THF	0
13	Cs₂CO₃	THF	0
14	Et₃N	THF	0
15	Pyridine	THF	0
16	t-BuOK	THF	86 ^c
17	t-BuOK	THF	85 ^d
18	t-BuOK	THF	58 ^e
19	t-BuOK	THF	60 ^f

Entry	Base	Solvent	Yield^b/%
1	t-BuOK	CH₂Cl₂	40
2	t-BuOK	THF	87
3	t-BuOK	1,4-Dioxane	58
4	t-BuOK	CH₃CN	41
5	t-BuOK	Toluene	17
6	t-BuOK	DMF	30
7	t-BuOK	Acetone	41
8	t-BuOK	DMSO	0
9	t-BuOK	DCE	0
10	t-BuONa	THF	36
11	K₂CO₃	THF	0
12	Na₂CO₃	THF	0
13	Cs₂CO₃	THF	0
14	Et₃N	THF	0
15	Pyridine	THF	0
16	t-BuOK	THF	86 ^c
17	t-BuOK	THF	85 ^d
18	t-BuOK	THF	58 ^e
19	t-BuOK	THF	60 ^f

t-BuOK促进的还原脱砜/脱氢反应: 选择性合成2-取代的1,3-共轭二烯及其应用

t-BuOK-Mediated Reductive Desulfonylation/Dehydrogenation for the Synthesis of 2-Substituted 1,3-Dienes and Their [4+2] Cycloaddition Reactions

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