Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2116-2120.DOI: 10.6023/cjoc202010008 Previous Articles Next Articles
NOTES
梁静茹1, 王冰莹1, 黄成尹1, 叶晓君1, 温燕梅1,*()
收稿日期:
2020-10-07
修回日期:
2020-12-16
发布日期:
2021-02-07
通讯作者:
温燕梅
作者简介:
基金资助:
Jingru Liang1, Bingying Wang1, Chengyin Huang1, Xiaojun Ye1, Yanmei Wen1,*()
Received:
2020-10-07
Revised:
2020-12-16
Published:
2021-02-07
Contact:
Yanmei Wen
About author:
Supported by:
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Jingru Liang, Bingying Wang, Chengyin Huang, Xiaojun Ye, Yanmei Wen. Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2116-2120.
[1] |
(a) Ramamoorthy, G.; Acevedo, C. M.; Alvira, E.; Lipton, M. A. Tetrahedron: Asymmetry 2008, 19, 2546.
doi: 10.1016/j.tetasy.2008.09.031 |
(b) Davis, R.; Kumar, N. S. S.; Abraham, S.; Suresh, C. H.; Rath, N. P.; Tamaoki, N.; Das, S. J. Phys. Chem. C 2008, 112, 2137.
doi: 10.1021/jp710352m |
|
(c) Xi, Z. F.; Zhang, W. X. Synlett 2008,2557.
|
|
(d) Amans, D.; Bellosta, V.; Cossy, J. Chem.-Eur. J. 2009, 15, 3457.
doi: 10.1002/chem.v15:14 |
|
(e) Huang, J. M.; Dong, Y.; Wang, X. X.; Luo, H. C. Chem. Commun. 2010, 46, 1035.
doi: 10.1039/b923464k |
|
(f) Zhou P.; Jiang H. F.; Huang L. B.; Li X. W. Chem. Commun. 2011, 47, 1003.
doi: 10.1039/C0CC03723K |
|
(g) Wen, Y. M.; Huang, L. B.; Jiang, H. F. J. Org. Chem. 2012, 77, 5418.
doi: 10.1021/jo300662x |
|
(h) Li, W. B.; Zhang, J. L. Org. Lett. 2014, 16, 162.
doi: 10.1021/ol4031556 |
|
(i) Jiang, B.; Zhao, M.; Li, S. S.; Xu, Y. H.; Loh, T. P. Angew. Chem., Int. Ed. 2018, 57, 555.
doi: 10.1002/anie.201710601 |
|
[2] |
(a) Lemhadri, M.; Battace, A.; Berthiol, F.; Zair, T.; Doucet, H.; Santelli, M. Synthesis 2008,1142.
|
(b) Blackwell, D. T.; Galloway, W. R. J. D.; Spring, D. R. Synlett 2011,2140.
|
|
(g) Yang, Q.; Chai, H.; Liu, T.; Yu, Z. Tetrahedron Lett. 2013, 54, 6485.
|
|
[3] |
(a) Phillips, A. M. F.; Pombeiro, A. J. L. ChemCatChem 2018, 10, 3354.
doi: 10.1002/cctc.201800582 |
(b) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
doi: 10.1021/ar800164n |
|
(c) Varun, B. V.; Dhineshkumar, J.; Bettadapur, K. R.; Siddaraju, Y.; Alagiri, K.; Prabhu, K. R. Tetrahedron Lett. 2017, 58, 803.
doi: 10.1016/j.tetlet.2017.01.035 |
|
(d) Wu, Y. N.; Wang, J.; Mao, F.; Kwong, F. Y. Chem.-Asian J. 2014, 9, 26.
doi: 10.1002/asia.201300990 |
|
(e) Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540.
|
|
(f) Lei, A. W.; Liu, W.; Liu, C.; Chen, M. Dalton Trans. 2010, 39, 10352.
doi: 10.1039/c0dt00486c |
|
(g) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170.
doi: 10.1021/cr100209d |
|
(h) Liu, C.; Yuan, J. W.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. W. Chem. Rev. 2015, 115, 12138.
doi: 10.1021/cr500431s |
|
(i) Murakami, K.; Yamada, S.; Kaneda, T.; Itami, K. Chem. Rev. 2017, 117, 9302.
doi: 10.1021/acs.chemrev.7b00021 |
|
(j) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
doi: 10.1021/cr100280d |
|
(k) Wang, C. S.; Dixneuf, P. H.; Soulé, J. F. Chem. Rev. 2018, 118, 7532.
doi: 10.1021/acs.chemrev.8b00077 |
|
(l) Li, X.; Ouyang, W., Nie, J.; Ji, S.; Chen, Q.; Huo, Y. ChemCatChem 2020, 12, 2358.
doi: 10.1002/cctc.v12.9 |
|
[4] |
(a) Wilklow-Marnell, M.; Li, B.; Zhou, T.; Krogh-Jespersen, K.; Brennessel, W. W.; Emge, T. J.; Goldman, A. S.; Jones, W. D. J. Am. Chem. Soc. 2017, 139, 8977.
doi: 10.1021/jacs.7b03433 |
(b) Sun, Q.; Cai, L.; Ding, Y.; Xie, L.; Zhang, C.; Tan, Q.; Xu, W. Angew. Chem., Intl. Ed. 2015, 54, 4549.
doi: 10.1002/anie.201412307 |
|
(c) Wen, Y.; Xie, J.; Deng, C.; Wu, Y. Synlett 2015, 26, 1755.
doi: 10.1055/s-00000083 |
|
[5] |
Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004.
pmid: 15926811 |
[6] |
(a) Jiang, H. F.; Qiao, C. L.; Liu, W. B. Chem.-Eur. J. 2010, 16, 10968.
doi: 10.1002/chem.v16:36 |
(b) Zhou P.; Jiang H. F.; Huang L. B. Chem. Commun. 2011, 47, 1003.
doi: 10.1039/C0CC03723K |
|
[7] |
Wen, Y. M.; Huang, L. B.; Jiang, H. F. J. Org. Chem. 2012, 77, 5418.
doi: 10.1021/jo300662x |
[8] |
Itami, K.; Ushiogi, Y.; Nokami, T.; Ohashi, Y.; Yoshida, J. Org. Lett. 2004, 6, 3695.
doi: 10.1021/ol048620i |
[9] |
Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
doi: 10.1021/ja00290a037 |
[10] |
Dhital, R. N.; Sakurai, H. Asian J. Org. Chem. 2014, 3, 668.
doi: 10.1002/ajoc.v3.6 |
[11] |
(a) Nagao, K.; Ohmiya, H.; Sawamura, M. Org. Lett. 2015, 17, 1304.
doi: 10.1021/acs.orglett.5b00305 |
(b) Verma, A.; Snead, R. F.; Dai, Y.; Slebodnick, C.; Yang, Y.; Yu, H.; Yao, F.; Santos, W. L. Angew. Chem., Int. Ed. 2017, 56, 5111.
doi: 10.1002/anie.201700946 |
|
(c) Kojima, C.; Lee, K.-H.; Lin, Z.; Yamashita, M. J. Am. Chem. Soc. 2016, 138, 6662.
doi: 10.1021/jacs.6b03686 |
|
(d) Morinaga, A.; Nagao, K.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2015, 54, 15859.
doi: 10.1002/anie.201509218 |
|
(e) Miralles, N.; Alam, R.; Szabó, K. J.; Fernández, E. Angew. Chem., Int. Ed. 2016, 55, 4303.
doi: 10.1002/anie.201511255 |
|
(f) Hong, S. B.; Zhang, W.; Liu, M. Y.; Yao, Z. J.; Deng, W. Tetrahedron Lett. 2016, 57, 1.
|
|
[12] |
Deng, C. M.; Ma, Y. F.; Wen, Y. M. ChemistrySelect 2018, 3, 1202.
doi: 10.1002/slct.201800038 |
[13] |
Zheng, C.; Wang, D.; Stahl, S. S. J. Am. Chem. Soc. 2012, 134, 16496.
doi: 10.1021/ja307371w |
[14] |
Thiel, N. O.; Kemper, S.; Teichert, J. F. Tetrahedron 2017, 73, 5023.
doi: 10.1016/j.tet.2017.05.029 |
[15] |
Hintermann, L.; Schmitz, M.; Chen, Y. Adv. Synth. Catal. 2010, 352, 2411.
doi: 10.1002/adsc.v352:14/15 |
[16] |
Al-Jawaheri, Y.; Kimber, M. Org. Lett. 2016, 18, 3502.
doi: 10.1021/acs.orglett.6b01841 |
[17] |
Zhuang, X.; Chen, J.-Y.; Yang, Z.; Jia, M.; Wu, C.; Liao, R.-Z.; Tung, C.-H.; Wang, W. Organometallics 2019, 38, 3752.
doi: 10.1021/acs.organomet.9b00486 |
[18] |
Parrish, J. P.; Jung, Y. C.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2002, 43, 7899.
doi: 10.1016/S0040-4039(02)01894-4 |
[19] |
Rodriguez, J. G.; Díaz-Oliva, C. Tetrahedron 2009, 65, 2512.
doi: 10.1016/j.tet.2009.01.050 |
[20] |
Ting, C.-M.; Hsu, Y.-L.; Liu, R.-S. Chem. Commun. 2012, 48, 6577.
doi: 10.1039/c2cc32131a |
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