钯催化羧基导向的C(sp2)—H键烷基化/环化合成2-(1-异色满酮-3-基)乙醛衍生物
收稿日期: 2024-10-22
修回日期: 2024-11-20
网络出版日期: 2024-11-25
基金资助
国家自然科学基金(21772070)
Palladium-Catalyzed Synthesis of 2-(1-Isochromen-3-yl)acetalde-hydes via Carboxyl-Directed C(sp2)—H Alkylation/Annulation
Received date: 2024-10-22
Revised date: 2024-11-20
Online published: 2024-11-25
Supported by
National Natural Science Foundation of China(21772070)
王悦 , 杨旭艳 , 刘添雨 , 李团结 , 张凯 , 姚昌盛 . 钯催化羧基导向的C(sp2)—H键烷基化/环化合成2-(1-异色满酮-3-基)乙醛衍生物[J]. 有机化学, 2024 , 44(11) : 3556 -3563 . DOI: 10.6023/cjoc202410013
A Pd(OAc)2-catalyzed efficient synthesis of 2-(1-isochromen-3-yl)acetaldehyde derivatives was achieved by the carboxyl-directed C—H bond alkylation/annulation of aryl acids with vinyl ethylene carbonate. This method has the advan- tages of ready availability of starting materials and operational simplicity, providing an alternative access to isochroman-1-one derivatives.
Key words: palladium acetate; aryl acid; vinyl ethylene carbonate; isochroman-1-one
| [1] | Barbier J.; Jansen R.; Irschik H.; Benson S.; Gerth K.; Bohlendorf B.; Hofle G.; Reichenbach H.; Wegner J.; Zeilinger C.; Kirschning A.; Muller R. Angew. Chem. Int. Ed. 2012, 51, 1256. |
| [2] | Cimmino A.; Maddau L.; Masi M.; Linaldeddu B. T.; Pescitelli G.; Evidente A. Chem. Biodiversity 2017, 14, e1700325. |
| [3] | Bai R.-R.; Xu S.-T.; Liu J.; Hong W.; Tang Y.-Q.; Wu X.-M.; Xie W.-J.; Yao H.-Q.; Xu J.-Y. Chin. J. Nat. Med. 2013, 11, 538. |
| [4] | Qian H.; Huang W. L.; Wu X. M.; Zhang H. B.; Zhou J. P.; Ye W. C. Chin. Chem. Lett. 2007, 18, 1227. |
| [5] | Das P.; Babbar P.; Malhotra N.; Sharma M.; Jachak G. R.; Gonnade R. G.; Shanmugam D.; Harlos K.; Yogavel M.; Sharma A.; Reddy D. S. J. Med. Chem. 2018, 61, 5664. |
| [6] | Fang B.; Xie X.; Zhao C.; Jing P.; Li H.; Wang Z.; Gu J.; She X. J. Org. Chem. 2013, 78, 6338. |
| [7] | Malir F.; Ostry V.; Pfohl-Leszkowicz A.; Malir J.; Toman J. Toxins 2016, 8, 191. |
| [8] | Kovács T.; Sonnenbichler J. Liebigs Ann. 1996, 1997, 211. |
| [9] | Matsuda H.; Wang Q.; Matsuhira K.; Nakamura S.; Yuan D.; Yoshikawa M. Phytomedicine 2008, 15, 177. |
| [10] | He J.; Wasa M.; Chan K. S. L.; Shao Q.; Yu J.-Q. Chem. Rev. 2017, 117, 8754. |
| [11] | Kumar G. S.; Chand T.; Singh D.; Kapur M. Org. Lett. 2018, 20, 4934. |
| [12] | Sun R.; Yang X.; Li Q.; Xu K.; Tang J.; Zheng X.; Yuan M.; Fu H.; Li R.; Chen H. Org. Lett. 2019, 21, 9425. |
| [13] | Jambu S.; Jeganmohan M. Org. Lett. 2020, 22, 5057. |
| [14] | Sheng R.; Li P.; Zhou Z.; Hu G.; Zhang X. Chin. J. Org. Chem. 2020, 40, 462 (in Chinese). |
| [14] | (圣戎, 李萍, 周志强, 胡贵文, 张小祥, 有机化学, 2020, 40, 462.) |
| [15] | Zhuang Z.; Herron A. N.; Liu S.; Yu J. Q. J. Am. Chem. Soc. 2021, 143, 687. |
| [16] | Jiang A.-L.; Zhou G.; Jiang B.-Y.; Zhou T.; Xu X.-T.; Shi B.-F. Org. Lett. 2024, 26, 5670. |
| [17] | Wang S.; Miao E.; Wang H.; Song B.; Huang W.; Yang W. Chem. Commun. 2021, 57, 5929. |
| [18] | Luo F. Chin. J. Org. Chem. 2019, 39, 3084 (in Chinese). |
| [18] | (罗飞华, 有机化学, 2019, 39, 3084.) |
| [19] | Chang M. -Y.; Chen S. -M.; Hsiao Y. -T. J. Org. Chem. 2019, 84, 11687-11698. |
| [20] | Tamanna T; Kumar M.; Joshi K.; Chauhan P. Adv. Synth. Catal. 2020, 362, 1907. |
| [21] | Yang X. C.; Xu M.; Wang J. B.; Liu M. M.; Mathey F.; Hua Y. Z.; Wang M. C. Org. Biomol. Chem. 2020, 18, 3917. |
| [22] | Zhang Y. H.; Shi B. F.; Yu J. Q. Angew. Chem. Int. Ed. 2009, 48, 6097. |
| [23] | Cheng G.; Li T.; Yu J-Q. J. Am. Chem. Soc. 2015, 137, 10950. |
| [24] | Nguyen T. T.; Grigorjeva L.; Daugulis O. Angew. Chem. Int. Ed. 2018, 57, 1688. |
| [25] | Zhang Y.; Wang H.; Bai J.; Liu Q.; Cui J.; Huang Y. Org. Lett. 2022, 24, 9222. |
| [26] | Liu S.-L.; Lv X.; Wang X.; Li Z.; Huang Q.; Jin Q.; Zhou L.; Fang S. J. Org. Chem. 2024, 89, 3672. |
| [27] | Niu B.; Wei Y.; Shi M. Org. Chem. Front. 2021, 8, 3475. |
| [28] | Li Y.; Li Y.; Dong Y.; Xia C.; Li Y. Chin. J. Org. Chem. 2022, 42, 847 (in Chinese). |
| [28] | (李玉东, 李莹, 董亚楠, 夏春谷, 李跃辉, 有机化学, 2022, 42, 847.) |
| [29] | Khan S.; Ahmad T.; Rasheed T.; Ullah N. Coord. Chem. Rev. 2022, 462, 214526. |
| [30] | Zhang S.-S.; Wu J.-Q.; Liu X.; Wang H. ACS Catal. 2015, 5, 210. |
| [31] | Lin C.; Gao Z.; Teng Q.; Xue B.; Li X.; Gao F.; Shen L. Chin. J. Org. Chem. 2020, 40, 2863 (in Chinese). |
| [31] | (林聪, 高震博, 腾秋汛, 薛博文, 李小花, 高飞, 申亮, 有机化学, 2020, 40, 2863.) |
| [32] | Cheng L.; Sun Y.; Wang W.; Yao C.; Li T.-J. J. Org. Chem. 2019, 84, 3074. |
| [33] | Wang W.; Fu X.; Cai Y.; Cheng L.; Yao C.; Wang X.; Li T.-J. J. Org. Chem. 2021, 86, 15423. |
| [34] | Li Z.; Wang Z.; Chekshin N.; Qian S.; Qiao J. X.; Cheng P. T.; Yeung K.-S.; Ewing W. R.; Yu J.-Q. Science 2021, 372, 1452. |
| [35] | Shinde D. B.; Kanth B. S.; Satyakumar |
/
| 〈 |
|
〉 |