无光催化剂条件下紫外光引发芳基醛或芳基酮与炔烃环化反应构筑茚酮化合物
收稿日期: 2021-07-07
修回日期: 2021-07-29
网络出版日期: 2021-08-10
基金资助
福建省中青年教师教育科研(JAT190990)
UV-Light-Initiated Construction of Indenones through Cyclization of Aryl Aldehydes or Aryl Ketones with Alkynes Avoiding Photocatalyst
Received date: 2021-07-07
Revised date: 2021-07-29
Online published: 2021-08-10
Supported by
Fujian Education and Scientific Research Project for Young and Middle-aged Teachers(JAT190990)
肖玉娟 , 杨阳 , 张凡 , 冯亚栋 , 崔秀灵 . 无光催化剂条件下紫外光引发芳基醛或芳基酮与炔烃环化反应构筑茚酮化合物[J]. 有机化学, 2021 , 41(12) : 4808 -4814 . DOI: 10.6023/cjoc202107021
The first UV-light-initiated cyclization of aryl aldehydes or aryl ketones with alkynes has been developed for the preparation of indenones. This reaction could proceed smoothly under UV-light with O2 as an oxidant and photocatalyst-free condition, which features high efficiency, high atom economy, easily available starting materials, environmental friendliness, and tolerance to broad functional groups.
Key words: UV-light; cyclization; photocatalyst-free; indenones
[1] | (a) Huebner, C. F.; Donoghue, E. M.; Plummer, A. J.; Furness, D. A. J. Med. Chem. 1966, 9, 830. |
[1] | (b) Jeffrey, J. L.; Sarpong, R. Org. Lett. 2009, 11, 5450. |
[1] | (c) Barbera, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem., Int. Ed. 1998, 37, 296. |
[1] | (d) Morinaka, K.; Ubukata, T.; Yokoyama, Y. Org. Lett. 2009, 11, 3890. |
[1] | (e) Anstead, G. M.; Wilson, S. R.; Katzenellenbogen, J. A. J. Med. Chem. 1989, 32, 2163. |
[1] | (f) Froimowitz, M.; Wu, K. M.; Moussa, A.; Haidar, R. M.; Jurayj, J.; George, C.; Gardner, E. L. J. Med. Chem. 2000, 43, 4981. |
[1] | (g) Gao, K.; Yoshikai, N. Chem. Commun. 2012, 48, 4305. |
[1] | (h) Kuninobu, Y.; Matsuki, T.; Takai, K. Org. Lett. 2012, 12, 2948. |
[1] | (i) Vasilyev, A. V.; Walspurger, S.; Pale, P.; Sommer, J. Tetrahedron Lett. 2004, 45, 3379. |
[1] | (j) Sheng, Y.; You, Y.; Cao, Z.; Liu, L.; Wu, H. C. Analyst 2018, 143, 2411. |
[2] | (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174. |
[2] | (b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. |
[2] | (c) Giri, R.; Shi, B.; Engle, K. M.; Maugel, N.; Yu, J. Chem. Soc. Rev. 2009, 38, 3242. |
[2] | (d) McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885. |
[2] | (e) Ylijoki, K. E. O.; Stryker, J. M. Chem. Rev. 2013, 113, 2244. |
[2] | (f) Wang, Z.; Xie, P.; Xia, X. Chin. Chem. Lett. 2018, 29, 47. |
[2] | (g) Zhang, Y.; Sun, K.; Lv, K.; Chen, X.; Qu, L.; Yu, B. Chin. Chem. Lett. 2019, 30, 1361. |
[2] | (h) Suo, J.; Du, J.; Jiang, Y.; Chen, D.; Ding, C.; Hou, X. Chin. Chem. Lett. 2019, 30, 1512. |
[2] | (i) Pan, Y.; Chen, G.; Shen, C.; He, W.; Ye, L. Org. Chem. Front. 2016, 3, 491. |
[2] | (j) Li, W.; Yin, G.; Huang, L.; Xiao, Y.; Fu, Z.; Xin, L.; Liu, F.; Li, Z.; He, W. Green Chem. 2016, 18, 4879. |
[2] | (k) Gao, Q.; Hao, W.; Liu, F.; Tu, S.; Wang, S.; Li, G.; Jiang, B. Chem. Commun. 2016, 52, 900. |
[2] | (l) Zhou, P.; Wang, J.; Zhang, T.; Li, G.; Hao, W.; Tu, S.; Jiang, B. Chem. Commun. 2018, 54, 164. |
[2] | (m) Zhu, S.; Zhou, J.; Wu, Q.; Hao, W.; Tu, S.; Jiang, B. Org. Chem. Front. 2020, 7, 2975. |
[2] | (n) Tian, S.; Luo, T.; Zhu, Y.; Wang, J. Chin. Chem. Lett. 2020, 31, 3072. |
[2] | (o) Butenschön, H. Angew. Chem., Int. Ed. 2008, 47, 5287. |
[2] | (p) Harmata, M. Chem. Commun. 2010, 46, 8886. |
[2] | (q) Lv, N.; Chen, Z.; Liu, Y.; Liu, Z.; Zhang, Y. Org. Lett. 2017, 19, 2588. |
[2] | (r) Yu, W.; Zhang, W.; Liu, Z.; Zhang, Y. Chem. Commun. 2016, 52, 6837. |
[3] | Chen, S.; Yu, J.; Jiang, Y.; Chen, F.; Cheng, J. Org. Lett. 2013, 15, 4754. |
[4] | Banerji, B.; Majumder, L.; Adhikary, S. ChemistrySelect 2018, 3, 1381. |
[5] | Feng, Y.; Zhang, H.; Yu, Y.; Yang, L.; Cui, X. Eur. J. Org. Chem. 2019, 16, 2740. |
[6] | (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. |
[6] | (b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. |
[6] | (c) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97. |
[7] | Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224. |
[8] | Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. J. Am. Chem. Soc. 2011, 133, 18566. |
[9] | (a) Tobisu, M.; Furukawa, T.; Chatani, N. Chem. Lett. 2013, 42, 1203. |
[9] | (b) Gomes, F.; Narbonne, V.; Blanchard, F.; Maestri, G. Org. Chem. Front. 2015, 2, 464. |
[9] | (c) Liang, L.; Xie, M.; Wang, H.; Niu, H.; Qu, G.; Guo, H. J. Org. Chem. 2017, 82, 966. |
[9] | (d) Xue, D.; Jia, Z.; Zhao, C.; Zhang, Y.; Wang, C.; Xiao, J. Chem.- Eur. J. 2014, 20, 2960. |
[9] | (e) Zhang, J.; Chen, J.; Zhang, X.; Lei, X. J. Org. Chem. 2014, 79, 10682. |
[9] | (f) Xu, H.; Jiang, Z. Chin. J. Org. Chem. 2020, 40, 3483. (in Chinese) |
[9] | ( 许荷欢, 江智勇, 有机化学, 2020, 40, 3483.) |
[9] | (g) Jin, J.-K.; Xia, H.-M.; Zhang, F.-L.; Wang, Y.-F. Chin. J. Org. Chem. 2020, 40, 2185. (in Chinese) |
[9] | ( 靳继康, 夏慧敏, 张凤莲, 汪义丰, 有机化学, 2020, 40, 2185.) |
[10] | Hari, D. P.; Schroll, P.; Ko?nig, B. J. Am. Chem. Soc. 2012, 134, 2958. |
[11] | (a) Huang, L.; Zhao, J. RSC Adv. 2013, 3, 23377. |
[11] | (b) Marzo, L.; Ghosh, I.; Esteban, F.; Konig, B. ACS Catal. 2016, 6, 6780. |
[11] | (c) Feng, Y; Bu, X.; Huang, B.; Rong, C.; Dai, J.; Xu, J.; Xu, H. Tetrahedron Lett. 2017, 58, 1939. |
[11] | (d) Kojima, M.; Oisaki, K. Kanai, M. Chem. Commun. 2015, 51, 9718. |
[11] | (e) Poelma, S. O.; Burnett, G. L.; Discekici, E. H.; Mattson, K. M.; Treat, N. J.; Luo, Y.; Hudson, Z. M.; Shankel, S. L.; Clark, P. G.; Kramer, J. W.; Hawker, C. J.; Read de Alaniz, J. J. Org. Chem. 2016, 81, 7155. |
[11] | (f) Cui, L.; Matusaki, Y.; Tada, N.; Miura, T.; Uno, B.; Itoh, A. Adv. Synth. Catal. 2013, 355, 2203. |
[12] | Vitale, A.; Bongiovanni, R.; Ameduri, B. Chem. Rev. 2015, 115, 8835. |
[13] | (a) Feng, Y.; Zhang, Z.; Fu, Q.; Yao, Q.; Huang, H.; Shen, J.; Cui, X. Chin. Chem. Lett. 2020, 31, 58. |
[13] | (b) Feng, Y.; Liu, Y.; Fu, Q.; Zou, Z.; Shen, J.; Cui, X. Chin. Chem. Lett. 2020, 31, 733. |
[13] | (c) Feng, Y.; Wu, Z.; Chen, T.; Fu, Q.; You, Q.; Shen, J.; Cui, X. Chin. Chem. Lett. 2020, 31, 3263. |
[13] | (d) Li, T.; Yang, Z.; Song, Z.; Chauvin, R.; Cui, X. Org. Lett. 2020, 22, 4078. |
[13] | (e) Liu, Y.; Yang, Z.; Chauvin, R.; Fu, W.; Yao, Z.; Wang, L.; Cui, X. Org. Lett. 2020, 22, 5140. |
[13] | (f) Yao, Z.; Lin, X.; Chauvin, R.; Wang, L.; Gras, E.; Cui, X. Chin. Chem. Lett. 2020, 31, 3250. |
[13] | (g) Song, Z.; Yang, Z.; Wang, P.; Shi, Z.; Li, T.; Cui, X. Org. Lett. 2020, 22, 6272. |
[13] | (h) Wu, Y.; Pi, C.; Cui, X.; Wu, Y. Org. Lett. 2020, 22, 361. |
[13] | (i) Ren, J.; Yan, X.; Cui, X.; Pi, C.; Wu, Y.; Cui, X. Green Chem. 2020, 22, 265. |
[13] | (j) He, Y.; Pi, C.; Wu, Y.; Cui, X. Chin. Chem. Lett. 2020, 31, 396. |
[13] | (k) Huang, Y.; Pi, C.; Cui, X.; Wu, Y. Adv. Synth. Catal. 2020, 362, 1385. |
[13] | (l) Wan, T.; Pi, C.; Wu, Y.; Cui, X. Org. Lett. 2020, 22, 6484. |
[13] | (m) Yu, H.; Pi, C.; Wang, Y.; Cui, X.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 124. (in Chinese) |
[13] | ( 余海洋, 皮超, 王勇, 崔秀灵, 吴养洁, 有机化学, 2018, 38, 124.) |
[13] | (n) Shi, Z.-J.; Wang, L.-H.; Cui, X. Chin. J. Org. Chem. 2019, 39, 1596. (in Chinese) |
[13] | ( 施兆江, 王连会, 崔秀灵, 有机化学, 2019, 39, 1596.) |
[14] | (a) Li, Z.; Li, D.; Wang, G. J. Org. Chem. 2013, 78, 10414. |
[14] | (b) Li, H.; Li, P.; Wang, L. Chem. Commun. 2013, 49, 9170. |
[14] | (c) Li, H.; Li, P.; Wang, L. Chem.-Eur. J. 2013, 19, 14432. |
[14] | (d) Wang, G.; Shang, R.; Cheng, W.; Fu, Y. Org. Lett. 2015, 17, 4830. |
[14] | (e) Ji, W.; Tan, H.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2016, 52, 1462. |
[14] | (f) Li, C.; Xu, G.; Xu, P. Org. Lett. 2017, 19, 512. |
[14] | (g) Xu, S.; Chen, J.; Liu, D.; Bao, Y.; Liang, Y.; Xu, P. Org. Chem. Front. 2017, 4, 1331. |
[14] | (h) Liu, Y.; Wang, Q.; Zhou, C.; Xiong, B.; Zhang, P.; Kang, S.; Yang, C.; Tang, K. Tetrahedron Lett. 2018, 59, 2038. |
[15] | (a) Sharma, U. K.; Gemoets, H. P. L.; Schroder, F.; Noel, T.; Eycken, E. V. ACS. Catal. 2017, 7, 3818. |
[15] | (b) Zhang, L.; Zhang, G.; Li, Y.; Wang, S.; Lei, A. Chem. Commun. 2018, 54, 5744. |
[15] | (c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991. |
[15] | (d) Yu, X.; Chen, J.; Chen, H.; Xiao, W.; Chen, J. Org. Lett. 2020, 22, 2333. |
[15] | (e) Zhao, Q.; Zhou, X.; Xu, S.; Wu, Y.; Xiao, W.; Chen, J. Org. Lett. 2020, 22, 2470. |
[15] | (f) Liang, D.; Tan, L.; Xiao, W.; Chen, J. Chem. Commun. 2020, 56, 3777. |
[15] | (g) Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 15, 6286. |
[15] | (h) Wertz, S.; Leifert, D.; Studer, A. Org. Lett. 2013, 15, 928. |
[16] | (a) Yi, R.; He, W. Chin. J. Org. Chem. 2021, 41, 1267. (in Chinese) |
[16] | ( 易荣楠, 何卫民, 有机化学, 2021, 41, 1267.) |
[16] | (b) Liu, R.; Yang, M.; Qiu, G.; Zhang, L.; Wang, Y.; Luo, J. Chin. J. Org. Chem. 2020, 40, 2071. (in Chinese) |
[16] | ( 刘仁志, 杨民, 邱观音生, 张莲鹏, 王玉超, 罗劲, 有机化学, 2020, 40, 2071.) |
[16] | (c) Peng, S.; Lin, Y.; He, W. Chin. J. Org. Chem. 2020, 40, 541. (in Chinese) |
[16] | ( 彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.) |
[16] | (d) Yuan, X.; Yang, G.; Yu, B. Chin. J. Org. Chem. 2020, 40, 3620. (in Chinese) |
[16] | ( 袁晓亚, 杨国平, 於兵, 有机化学, 2020, 40, 3620.) |
[16] | (e) Wu, Y.; Chen, J.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W. Green Chem. 2021, 23, 3950. |
[16] | (f) Jiang, J.; Xiao, F.; He, W.; Wang, L. Chin. Chem. Lett. 2021, 32, 1637. |
[16] | (g) He, W.; Gao, L.; Chen, X.; Wu, Z.; Huang, Y.; Cao, Z.; Xu, X.; He, W. Chin. Chem. Lett. 2020, 31, 1895. |
[17] | Tsukamoto, H.; Kondo, Y. Org. Lett. 2007, 21, 4227. |
[18] | Feng, Y.; Zhang, H.; Yu, Y.; Yang, L.; Cui, X. Eur. J. Org. Chem. 2019, 16, 2740. |
[19] | Zhang, J.; Yang, F.; Wu, Y. Appl. Organomet. Chem. 2011, 25, 675. |
[20] | Jafarpour, F.; Azizzade, M.; Golpazir-Sorkheh, Y.; Navid, H.; Rajai- Daryasarei, S. J. Org. Chem. 2020, 85, 8287. |
[21] | Curtin, D. Y.; Johnson, H. W., Jr.; Steiner, E. G. J. Am. Chem. Soc. 1955, 77, 4566. |
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