BCl3 Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones

doi:10.6023/cjoc202005025

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3908-3915.DOI: 10.6023/cjoc202005025 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化

吴毅^a, 肖元晶^a, 张俊良^a,b

a 华东师范大学化学与分子工程学院上海市绿色化学与化学工程绿色化重点实验室上海 200062;
b 复旦大学化学系上海 200438

收稿日期:2020-05-10 修回日期:2020-06-08 发布日期:2020-07-01
通讯作者: 肖元晶, 张俊良 E-mail:yjxiao@chem.ecnu.edu.cn;jlzhang@chem.ecnu.edu.cn
基金资助:
国家自然科学基金（Nos.21372084，21425205，21871093）、教育部长江学者和创新团队发展计划和国家重点基础研究发展计划（973计划，No.2015CB-856600）资助项目.

BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones

Wu Yi^a, Xiao Yuanjing^a, Zhang Junliang^a,b

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b Department of Chemistry, Fudan University, Shanghai 200438

Received:2020-05-10 Revised:2020-06-08 Published:2020-07-01
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372084, 21425205, 21871093), the Program for Changjiang Scholars and Innovative Research Team in University of Ministry of Education and the National Basic Research Program of China (973 Program, No. 2015CB-856600).

1. cjoc202005025辅助材料.pdf(1781KB)

Abstract

A metal-free, BCl₃ mediated borylative cyclization of 2-(1-alkynyl)-2-alken-1-ones leading to synthetic valuable multi-functionalized naphthalene boronates in one step was developed. The boronate functionality present in the product provides many opportunities for derivatization. The salient features of this reaction include moderate to good yields, gram-scale synthesis and diverse synthetic transformations. In the meantime, the new synthetic applications of 2-(1-alkynyl)-2-alken-1-ones have been developed.

Key words: metal free, borylative, cycliazation, naphthalene boronates, transformations

Cite this article

Wu Yi, Xiao Yuanjing, Zhang Junliang. BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3908-3915.

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References

[1] (a) Ward, R. S. Nat. Prod. Rep. 1995, 12, 183. (b) Thomson, R. H. Naturally Occurring Quinones IV. Recent Advances, 4th ed. Chapman & Hall, London, 1997.
(c) Liu, X. L.; Zhao, Y.; Wang, W. W.; Wang, M. A.; Zhou, L. G. Chin. J. Org. Chem. 2017, 37, 2883(in Chinese). (刘鑫磊, 赵宇, 王卫伟, 王明安, 周立刚, 有机化学, 2017, 37, 2883.)
[2] (a) Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452. (b) Reddy, R. A.; Baumeister, U.; Keith, C.; Tschierske, C. J. Mater. Chem. 2007, 17, 62.
(c) Svoboda, J.; Novotna, V.; Kozmik, V.; Glogarova, M.; Weissflog, W.; Diele, S.; Pelzl, G. J. Mater. Chem. 2003, 13, 2104.
(d) Christian, J.; Susann, G.; Helmut, H.; Brigitte, S. Naphthalene Compounds for Liquid-Crystalline Mixtures, WO 2017097400 A1.
[3] For selected reviews:(a) Zhou, L.; Zhao, J.; Shan, T.; Cai, X.; Peng, Y. Mini-Rev. Med. Chem. 2010, 10, 977.
(b) Ammar, Y. A.; Salem, M. A.; Fayed, Eman A.; Helal, M. H.; El-Gaby, M. S. A.; Thabet, H. K. Syn. Commun. 2017, 47, 1341. For selected examples:
(c) Zhao, H.; Neamati, N.; Mazumder, A.; Sunder, S.; Pommier, Y.; Burke, T. R. J. Med. Chem. 1997, 40, 1186.
(d) Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamto, Y.; Takahashi, M.; Kotera, J.; Ikeo, T. J. Med. Chem. 1999, 42, 1293.
(e) Wang, Y. H.; Zhao, J. Y. WO 2017202207, 2017.
[4] For reviews:(a) Naphthalenes, Anthracenes, 9H-Fluorenes, and Other Acenens, Toyota, S.; Iwanaga, T. in Science of Synthesis (Houben-Weyl Methods of Molecular Transformations), Eds.:Siegel, J. S.; Tobe, Y., Vol. 45b, Thieme, Stuttgart, 2010, pp. 745~854.
(b) de Koning, C. B.; Rousseau, A. L.; van Otterlo, W. A. L. Tetrahedron 2003, 59, 7.
(c) Hein, S. J.; Lehnherr, D.; Arslan, H.; Uribe-Romo, F. J.; Dichtel, W. R. Acc. Chem. Res. 2017, 50, 2776.
[5] (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
(c) Miyaura, N. Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Halides in Metal-Catalyzed Cross-Coupling Reactions (Eds. A. de Meijere, F. Diederich), WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004.
(d) Li, Y.; Wang, Z. H. Org. Lett. 2009, 11, 1385.
(e) Heffernan, G. D.; Jacobus, D. P.; Schiehser, G. A.; Shieh, H.-M.; Zhao, W. Preparation of Aryl Derivatives as Antimalarial Agents, WO 2014074778A1.
(f) Kikuchi, Y.; Takahagi, H.; One, K.; Iwasawa, N. Chem. Asian J. 2014, 9, 1001.
(g) Wang, Y. B.; Lin, Z. C.; Fan, H. L.; Peng, X. H. Chem. Eur. J. 2016, 22, 10382.
[6] Hall, D. Boronic Acids:Preparation and Applications, Wiley-VCH, Weinheim, 2011.
[7] For reviews, see:(a) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3.
(b) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. C.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
[8] For recent selected examples:
(c) Yamamoto, T.; Morita, T.; Takagi, J.; Yamakawa, T. Org. Lett. 2011, 13, 5766.
(d) Tang, W. J.; Keshipeddy, S.; Zhang, Y. D.; Wei, X. D.; Savoie, J. Patel, N. D.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2011, 13, 1366.
(e) Ros, A.; Estepa, B.; López-Rodríguez, R.; Álvarez, E.; Fernández, R.; Lassaletta, J. M. Angew. Chem., Int. Ed. 2011, 50, 11724.
(f) Kawamorita, S.; Ohmiya, H.; Iwai, T.; Sawamura, M. Angew. Chem., Int. Ed. 2011, 50, 8363.
(g) Kawamorita, S.; Miyazaki, T.; Ohmiya, H.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2011, 133, 19310.
(h) Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 134.
(i) Jiang, M.; Yang, H. J.; Fu, H. Org. Lett. 2016, 18, 5248.
(j) Xu, Y. L.; Fang, H. Chin. J. Org. Chem. 2018, 38, 738(in Chinese). (徐玉良, 方浩, 有机化学, 2018, 38, 738.)
[9] (a) Yamamoto, E.; Izumi, K.; Horita, Y.; Ito, H. J. Am. Chem. Soc. 2012, 134, 19997.
(b) Yamamoto, E.; Ukigai, S.; Ito, H. Chem. Sci. 2015, 6, 2943.
(c) Mo, F. Y.; Jiang, Y. B.; Qiu, D.; Zhang, Y.; Wang, J. B. Angew. Chem., Int. Ed. 2010, 49, 1846.
[10] For reviews:(a) Wrackmeyer, B. Heteroat. Chem. 2006, 17, 188.
(b) Melen, R. L. Chem. Commun. 2014, 50, 1161.
(c) Buñuel, E.; Cárdenas, D. J. Eur. J. Org. Chem. 2016, 5446.
(d) Issaian, A.; Tu, K. N.; Blum, S. A. Acc. Chem. Res. 2017, 50, 2598. For selected recent examples:
(e) Yang, C.-H.; Zhang, Y.-S.; Fan, W.-W.; Liu, G.-Q.; Li, Y.-M. Angew. Chem., Int. Ed. 2015, 54, 12636.
(f) Faizi, D. J.; Issaian, A.; Davis, A. J.; Blum, S. A. J. Am. Chem. Soc. 2016, 138, 2126.
(g) Jiang, J. L.; Zhang, Z. Q.; Fu, Y. Asian J. Org. Chem. 2017, 6, 282.
(h) Yuan, K.; Wang, S.-N. Org. Lett. 2017, 19, 1462.
(i) Warner, A. J.; Churn, A.; McGough, J. S.; Ingleson, M. J. Angew. Chem., Int. Ed. 2017, 56, 354.
(j) Kubota, K.; Yamamoto, E.; Ito, H. J. Am. Chem. Soc. 2013, 135, 2635.
(k) Jiang, T.; Bartholomeyzik, T.; Mazuela, J.; Willersinn, J.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2015, 54, 6024.
(l) Yu, S. J.; Wu, C. Z.; Ge, S. Z. J. Am. Chem. Soc. 2017, 139, 6526.
(m) Zuo, Y.-J.; Chang, X.-T.; Hao, Z.-M.; Zhong, C.-M. Org. Biomol. Chem. 2017, 15, 6323.
(n) Wang, H.-M.; Zhou, H.; Xu, Q.-S.; Liu, T.-S.; Zhuang, C.-L.; Shen, M.-H.; Xu, H.-D. Org. Lett. 2018, 20, 1777.
(o) Lv, J. H; Zhao, B. L.; liu, L.; Han, Y.; Yuan, Y.; Shi, Z. Z. Adv. Synth. Catal. 2018, 360, 4054.
[11] Liedtke, R.; Harhausen, M.; Fröhlich, R.; Kehr, G.; Erker, G. Org. Lett. 2012, 14, 1448.
[12] Warner, A. J.; Lawson, J. R.; Fasano, V.; Ingleson, M. J. Angew. Chem., Int. Ed. 2015, 54, 11245.
[13] For selected examples from our group's work, please see:(a) Xiao, Y. J.; Zhang, J. L. Angew. Chem., Int. Ed. 2008, 47, 1903.
(b) Liu, F.; Yu, Y. H.; Zhang, J. L. Angew. Chem., Int. Ed. 2009, 48, 5505.
(c) Liu, F.; Qian, D. Y.; Li, L.; Zhao, X. L.; Zhang, J. L. Angew. Chem., Int. Ed. 2010, 49, 6669.
(d) Zhou, L. J.; Zhang, M. R.; Li, W. B.; Zhang, J. L. Angew. Chem., Int. Ed. 2014, 53, 6542.
(e) Zhang, Z.-M.; Chen, P.; Li, W. B.; Niu, Y. F.; Zhao, X. L.; Zhang, J. L. Angew. Chem., Int. Ed. 2014, 53, 4350.
(f) Wang, Y. D.; Zhang, P. C.; Qian, D. Y.; Zhang, J. L. Angew. Chem., Int. Ed. 2015, 54, 14849.
[14] For selected recent examples from other group's work, please see:(a) Pathipati, S. R.; van der Werf, A.; Eriksson, L.; Selander, N. Angew. Chem., Int. Ed. 2016, 55, 11863.
(b) Kumari, A. L. S.; Swamy, K. C. K. J. Org. Chem. 2016, 81, 1425.
(c) Zhang, H.; Yao, Q.; Lin, L. L.; Xu, C. R.; Liu, X. H.; Feng, X. M. Adv. Synth. Catal. 2017, 359, 3454.
(d) Pathipati, S. R.; Eriksson, L.; Selander, N. Chem. Commun. 2017, 53, 11353.
(e) Liu, S. N.; Yang, P.; Peng, S. Y.; Zhu, C. H.; Cao, S. Y.; Li, J.; Sun, J.-T. Chem. Commun. 2017, 53, 1152.
(f) Zheng, Y.; Chi, Y. J.; Bao, M.; Qiu, L. H.; Xu, X. F. J. Org. Chem. 2017, 82, 2129.
(g) Du, Q. W.; Neudçrfl, J.-M.; Schmalz, H.-G. Chem. Eur. J. 2018, 24, 2379.
(h) Kardile, R. D.; Chao, T.-H.; Cheng, M.-J.; Liu, R.-S. Angew. Chem., Int. Ed. 2020, 59, 1.
[15] X-ray data and ORTEP depiction for compounds 3b (CCDC 1870210).
[16] Zhou, H.; Moberg, C. J. Am. Chem. Soc. 2012, 134, 15992.
[17] Lv, J. H.; Zhao, B. L.; Yuan, Y.; Han, Y.; Shi, Z. Z. Nat. Commun. 2020, 11, 1316.
[18] (a) Yao, T. L.; Zhang, X. X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164.
(b) Yao, T. L.; Zhang, X. X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679.
(c) Liu, Y. H.; Zhou, S. L. Org. Lett. 2005, 7, 4609.
[19] Thompson, A. L. S.; Kabalka, G. W.; Akula, M. R.; Huffman, J. W. Synthesis 2005, 36, 547.
[20] Nakanishi, W.; Matsuyama, N.; Hara, D.; Saeki, A.; Hitosugi, S.; Seki, S.; Isobe, H. Chem. Asian J. 2014, 9, 1782.
[21] Li, Y.; Gao, L. X.; Han, F. S. Chem. Eru. J. 2010, 16, 7969.
[22] Yao, W. B. CN 107188773, 2017.

三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化

BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones

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