Chinese Journal of Organic Chemistry >
Syntheses and Structural Characterizations of Benzoxazolyl N-Heterocyclic Carbene-Palladium Complexes and Their Applications
Received date: 2023-11-14
Revised date: 2024-01-29
Online published: 2024-02-28
Supported by
National Natural Science Foundation of China(22071171); Natural Science Foundation of Zhejiang Province(LZ22B020003)
Six seven-membered benzoxazolyl N-heterocyclic carbene (Benzoxa^NHC) palladium complexes with flexible linear alkyl or benzyl linkers were synthesized. Their structures were characterized by NMR, HRMS, and FTIR spectroscopies. The structures of three complexes were further confirmed by X-ray single crystal diffraction. Palladium center adopted slight distorted square planer geometry, and the benzoxazole and NHC planes in its ligand formed a certain angle with each other, not coplanar. The first methylene group connected to a nitrogen-containing heterocyclic carbene fragment exhibited magnetic anisotropy in the complex. The shift difference in the methylene group (Δδg) changed with the increase of the length of the side chain. When the side chain was a linear chain alkyl group of four carbons, Δδg reched maximum. Furthermore, these complexes showed excellent catalytic performance in Suzuki-Miyaura coupling, and could be used to synthesize biphenyl gem-difluoroethenes in the manner of two steps in one pot.
Chao Sun , Quan Zhou , Chuanying Li , Lei Wang . Syntheses and Structural Characterizations of Benzoxazolyl N-Heterocyclic Carbene-Palladium Complexes and Their Applications[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1957 -1966 . DOI: 10.6023/cjoc202311013
| [1] | Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361. |
| [2] | (a) Nolan, S. P. Angew. Chem., Int. Ed. 2015, 127, 5916. |
| [2] | (b) Anju, P. J.; Neetha, M.; Anilkumar, G. ChemistrySelect 2022, 7, e202103564. |
| [2] | (c) Budagumpi, S.; Haque, R. A.; Salman, A. W. Coord. Chem. Rev. 2012, 256, 1787. |
| [2] | (d) Gautam, A.; Shahini, C. R.; Siddappa, A. P.; Jan Grzegorz, M.; Hemavathi, B.; Ahipa, T. N.; Srinivasa, B. J. Organomet. Chem. 2021, 934, 121540. |
| [2] | (e) Astakhov, A. V.; Khazipov, O. V.; Chernenko, A. Y.; Pasyukov, D. V.; Kashin, A. S.; Gordeev, E. G.; Khrustalev, V. N.; Chernyshev, V. M.; Ananikov, V. P. Organometallics 2017, 36, 1981. |
| [2] | (f) Shao, H.; Ma, Y.; Lin, T.; Li, W.; Deng, Q. Asian J. Org. Chem. 2023, 12, e202300064. |
| [2] | (g) Sau, S. C.; Hota, P. K.; Mandal, S. K.; Soleilhavoup, M.; Bertrand, G. Chem. Soc. Rev. 2020, 49, 1233. |
| [2] | (h) Li, J.; He, D.; Lin, Z.; Wu, W.; Jiang, H. Org. Chem. Front. 2021, 8, 3502. |
| [3] | Würtz, S.; Lohre, C.; Fr?hlich, R.; Bergander, K.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 8344. |
| [4] | Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195. |
| [5] | Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485. |
| [6] | Gyton, M. R.; Leforestier, B.; Chaplin, A. B. Organometallics 2018, 37, 3963. |
| [7] | (a) Luo, W.-Q.; Du, X.-G.; Chen, L.-Y.; Jin, C.-M. J. Organometal. Chem. 2021, 952, 122033. |
| [7] | (b) Peng, H. M.; Song, G.; Li, Y.; Li, X. Inorg. Chem. 2008, 47, 8031. |
| [8] | Wang, R.; Twamley, B.; Shreeve, J. M. J. Org. Chem. 2006, 71, 426. |
| [9] | Sie, M.-H.; Hsieh, Y.-H.; Tsai, Y.-H.; Wu, J.-R.; Chen, S.-J.; Lii, J.-H.; Lee, H. M. Organometallics 2010, 29, 6473. |
| [10] | Turek, J.; Panov, I.; Semler, M.; ?těpni?ka, P.; De Proft, F.; Padělková, Z.; R??i?ka, A. Organometallics 2014, 33, 3108. |
| [11] | (a) Ammar, H. B.; Hassine, B. B.; Fischmeister, C.; Dixneuf, P. H.; Bruneau, C. Eur. J. Inorg. Chem. 2010, 2010, 4752. |
| [11] | (b) Hoffmann, M.; Dagorne, S.; Pale, P.; Blanc, A.; de Frémont, P. J. Organomet. Chem. 2022, 979, 122507. |
| [11] | (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162. |
| [12] | (a) El Hatimi, A.; Gómez, M.; Jansat, S.; Muller, G.; Font-Bardía, M.; Solans, X. J. Chem. Soc., Dalton Trans. 1998, 4229. |
| [12] | (b) Viciano, M.; Feliz, M.; Corberán, R.; Mata, J. A.; Clot, E.; Peris, E. Organometallics 2007, 26, 5304. |
| [12] | (c) Wanniarachchi, Y. A.; Kogiso, Y.; Slaughter, L. M. Organometallics 2008, 27, 21. |
| [13] | Huang, S.; Hong, X.; Cui, H.-Z.; Zhan, B.; Li, Z.-M.; Hou, X.-F. Organometallics 2020, 39, 3514. |
| [14] | (a) Huang, S.; Wu, S.-P.; Zhou, Q.; Cui, H.-Z.; Hong, X.; Lin, Y.-J.; Hou, X.-F. J. Organomet. Chem. 2018, 868, 14. |
| [14] | (b) Huang, S.; Hong, X.; Cui, H.-Z.; Zhou, Q.; Lin, Y.-J.; Hou, X.-F. Dalton Trans. 2019, 48, 5072. |
| [15] | (a) Zhou, Q.; Hong, X.; Cui, H.-Z.; Huang, S.; Yi, Y.; Hou, X.-F. J. Org. Chem. 2018, 83, 6363. |
| [15] | (b) Zhou, Q.; Liu, S.; Ma, M.; Cui, H.-Z.; Hong, X.; Huang, S.; Zhang, J.-F.; Hou, X.-F. Synthesis 2018, 50, 1315. |
| [15] | (c) Shen, M. H.; Li, L. Q.; Zhou, Q.; Wang, J. H.; Wang, L. Chin. J. Org. Chem. 2023, 43, 697. (in Chinese) |
| [15] | (沈梦涵, 李来强, 周泉, 王洁慧, 王磊, 有机化学, 2023, 43, 697.) |
| [15] | (d) Zhou, Q.; Yu, H. Y.; Zhou, Y. Q.; Wei, J. R.; Wang, L. Org. Biomol. Chem. 2022, 20, 5575. |
| [16] | Almy, J.; Martinez Alverez, R.; Fernandez, A. H.; Vazquez, A. S. J. Chem. Educ. 1997, 74, 1479. |
| [17] | Minghetti, G.; Cinellu, M. A.; Bandini, A. L.; Banditelli, G.; Demartin, F.; Manassero, M. J. Organometal. Chem. 1986, 315, 387. |
| [18] | Sugiyama, T.; Meng, J.; Matsuura, T. Acta Crystallogr.,Sect. C: Struct. Chem. 2002, 58, o242. |
| [19] | Chen, W.; Chen, K.; Chen, W.; Liu, M.; Wu, H. ACS Catal. 2019, 9, 8110. |
| [20] | Zhou, J.; Luo, S.; Liu, H.; Xue, P. J. Organomet. Chem. 2022, 965-966, 122323. |
| [21] | Pauling, L. J. Chem. Educ. 1992, 69, 519. |
| [22] | Sugiyama, T.; Meng, J. B.; Matsuura, T. Acta Crystallogr., Sect. C: Struct. Chem. 2002, 58, 242. |
| [23] | Chakrabortty, S.; Kaur, M.; Adhikari, M.; Manar, K. K.; Singh, S. Inorg. Chem. 2021, 60, 6209. |
| [24] | (a) Pan, S.; Song, M.; Zuo, L.; Geng, X.; Wang, L. J. Org. Chem. 2023, 88, 5586. |
| [24] | (b) Xu, Z.; Geng, X.; Cai, Y.; Wang, L. J. Org. Chem. 2022, 87, 6562. |
| [24] | (c) Huo, J.; Geng, X.; Li, W.; Zhang, P.; Wang, L. Org. Lett. 2023, 25, 512. |
| [24] | (d) Zhang, J.-Q.; Hu, D.; Wang, J.; Ni, B.; Ren, H. Org. Lett. 2022, 24, 7905. |
| [24] | (e) Zhang, J.-Q.; Liu, J.; Hu, D.; Song, J.; Zhu, G.; Ren, H. Org. Lett. 2022, 24, 786. |
| [24] | (f) Hou, Z.-W.; Jiang, T.; Wu, T.-X.; Wang, L. Org. Lett. 2021, 23, 8585. |
| [24] | (g) Li, J.-S.; Liu, Y.-J.; Zhang, G.-W.; Ma, J.-A. Org. Lett. 2017, 19, 6364. |
| [24] | (h) Pan, Z.; Wang, X.; Zhao, S.; Deng, H.; Ma, M.; Xue, F. Org. Lett. 2023, 25, 6143. |
| [24] | (i) Sun, J.; Miao, T.; Li, P.; Wang, L. Chin. J. Org. Chem. 2021, 41, 3144. (in Chinese) |
| [24] | (孙佳兵, 苗涛, 李品华, 王磊, 有机化学, 2021, 41, 3144.) |
| [24] | (j) Gao, R.; Zuo, L.; Wang, F.; Li, C.; Jiang, H.; Li, P.; Wang, L. Chin. J. Org. Chem. 2022, 42, 1883. |
| [24] | (k) He, H.; Lv, Y.; Hu, J.; Hou, Z.-W.; Wang, L. Green Chem. 2024, 26, 2157. |
| [24] | (l) Sun, C.; Zhou, Q.; Li, C.-Y.; Hou, Z.-W.; Wang, L. Org. Lett. 2024, 26, 883. |
| [24] | (m) Zhang, Z.; Zhou, Y.; Wang, J.; Zhang, Y.; Wang, L.; Liu, J.; Zhou, C.; Wang, M.; Li, P. Org. Biomol. Chem. 2024, 22, 1708. |
| [24] | (n) Hou, Z.-W.; Xu, H.-C.; Wang, L. Curr. Opin. Electrochem. 2024, 44, 101447. |
| [25] | Sakaguchi, H.; Uetake, Y.; Ohashi, M.; Niwa, T.; Ogoshi, S.; Hosoya, T. J. Am. Chem. Soc. 2017, 139, 12855. |
| [26] | King, R. P.; Krska, S. W.; Buchwald, S. L. Org. Lett. 2021, 23, 7927. |
| [27] | (a) Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339. |
| [27] | (b) Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Acta Crystallogr.,Sect. A: Found. Adv. 2015, 71, 59. |
| [28] | Sheldrick, G. M. Acta Crystallogr.,Sect. C: Struct. Chem. 2015, 71, 3. |
/
| 〈 |
|
〉 |
