Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3264-3271.DOI: 10.6023/cjoc202103038 Previous Articles Next Articles
ARTICLES
许振丽a, 张宗雪b, 孟晨湘b, 张萧雅b, 许凯b,*(), 刘澜涛b,c, 王涛b, 徐海云b, 毛国梁a,*()
收稿日期:
2021-03-22
修回日期:
2021-04-13
发布日期:
2021-05-08
通讯作者:
许凯, 毛国梁
基金资助:
Zhenli Xua, Zongxue Zhangb, Chenxiang Mengb, Xiaoya Zhangb, Kai Xub(), Lantao Liub,c, Tao Wangb, Haiyun Xub, Guoliang Maoa()
Received:
2021-03-22
Revised:
2021-04-13
Published:
2021-05-08
Contact:
Kai Xu, Guoliang Mao
Supported by:
Share
Zhenli Xu, Zongxue Zhang, Chenxiang Meng, Xiaoya Zhang, Kai Xu, Lantao Liu, Tao Wang, Haiyun Xu, Guoliang Mao. Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3264-3271.
Entry | Catalyst | Base | Additive | Solvent | Yieldb/% |
---|---|---|---|---|---|
1 | Pd(OAc)2 | KOH | No | EtOH | 43 |
2 | Pd(OAc)2 | K2CO3 | No | EtOH | 18 |
3 | Pd(OAc)2 | K3PO4 | No | EtOH | 63 |
4 | Pd(OAc)2 | KF | No | EtOH | 67 |
5 | Pd(OAc)2 | Pyridine | No | EtOH | <5 |
6 | Pd(OAc)2 | NEt3 | No | EtOH | 68 |
7 | Pd(OAc)2 | nBu3N | No | EtOH | 85 |
8c | Pd(OAc)2 | nBu3N | No | EtOH | 78 |
9 | PdCl2 | nBu3N | No | EtOH | 43 |
10 | NiCl2 | nBu3N | No | EtOH | <5 |
11 | Pd(OAc)2 | nBu3N | No | iPrOH | 17 |
12 | Pd(OAc)2 | DBU | No | iPrOH | <5 |
13 | Pd(OAc)2 | KOH | No | iPrOH | 67 |
14 | Pd(OAc)2 | K2CO3 | No | iPrOH | 79 |
15 | Pd(OAc)2 | KOAc | No | iPrOH | 48 |
16 | Pd(OAc)2 | K3PO4 | No | iPrOH | 64 |
17 | Pd(OAc)2 | KF | No | iPrOH | 66 |
18 | PdCl2 | K2CO3 | No | iPrOH | 24 |
19 | NiCl2 | K2CO3 | No | iPrOH | <5 |
20 | Pd(OAc)2 | K2CO3 | TBAB | iPrOH | 83 |
Entry | Catalyst | Base | Additive | Solvent | Yieldb/% |
---|---|---|---|---|---|
1 | Pd(OAc)2 | KOH | No | EtOH | 43 |
2 | Pd(OAc)2 | K2CO3 | No | EtOH | 18 |
3 | Pd(OAc)2 | K3PO4 | No | EtOH | 63 |
4 | Pd(OAc)2 | KF | No | EtOH | 67 |
5 | Pd(OAc)2 | Pyridine | No | EtOH | <5 |
6 | Pd(OAc)2 | NEt3 | No | EtOH | 68 |
7 | Pd(OAc)2 | nBu3N | No | EtOH | 85 |
8c | Pd(OAc)2 | nBu3N | No | EtOH | 78 |
9 | PdCl2 | nBu3N | No | EtOH | 43 |
10 | NiCl2 | nBu3N | No | EtOH | <5 |
11 | Pd(OAc)2 | nBu3N | No | iPrOH | 17 |
12 | Pd(OAc)2 | DBU | No | iPrOH | <5 |
13 | Pd(OAc)2 | KOH | No | iPrOH | 67 |
14 | Pd(OAc)2 | K2CO3 | No | iPrOH | 79 |
15 | Pd(OAc)2 | KOAc | No | iPrOH | 48 |
16 | Pd(OAc)2 | K3PO4 | No | iPrOH | 64 |
17 | Pd(OAc)2 | KF | No | iPrOH | 66 |
18 | PdCl2 | K2CO3 | No | iPrOH | 24 |
19 | NiCl2 | K2CO3 | No | iPrOH | <5 |
20 | Pd(OAc)2 | K2CO3 | TBAB | iPrOH | 83 |
[1] |
For reviews: see:
pmid: 27787975 |
(a) Moonen, K.; Laureyn, O.; Stevens, C. V. Chem. Rev. 2004, 104, 6177.
doi: 10.1021/cr030451c pmid: 27787975 |
|
(b) Demmer, C. S.; Larsen, N. K.; Bunch, L. Chem. Rev. 2011, 111, 7981.
doi: 10.1021/cr2002646 pmid: 27787975 |
|
(c) Queffelec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777.
doi: 10.1021/cr2004212 pmid: 27787975 |
|
(d) Galezowska, J.; Gumienna-Kontecka, E. Coord. Chem. Rev. 2012, 256, 105.
doi: 10.1016/j.ccr.2011.07.002 pmid: 27787975 |
|
(e) Soller, B. S.; Salzinger, S.; Rieger, B. Chem. Rev. 2016, 116, 1993.
doi: 10.1021/acs.chemrev.5b00313 pmid: 27787975 |
|
(f) Horsman, G. P.; Zechel, D. L. Chem. Rev. 2017, 117, 5704.
doi: 10.1021/acs.chemrev.6b00536 pmid: 27787975 |
|
(g) Shi, B. C.; Fang, Y. W.; Zhang, L.; Jin, X. P.; Wu, Y. H.; Fang, M.; Yang, Y. F.; Chen, C. Chin. J. Org. Chem. 2016, 36, 673. (in Chinese)
pmid: 27787975 |
|
(方烨汶, 张莉, 金小平, 武永辉, 方媚, 杨宇飞, 陈冲, 有机化学, 2016, 36, 673.)
pmid: 27787975 |
|
(h) Ye, X. Y.; Peng, L.; Bao, X. Z.; Tan, C. H.; Wang, H. Green Synth. Catal. 2021, 2, 6.
pmid: 27787975 |
|
[2] |
(a) Michaelis, A.; Kaehne, R. Ber. Dtsch. Chem. Ges. 1898, 31, 1048.
doi: 10.1002/(ISSN)1099-0682 pmid: 28686460 |
(b) Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687.
pmid: 28686460 |
|
(c) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 3595.
doi: 10.1016/0040-4039(80)80245-0 pmid: 28686460 |
|
(d) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
doi: 10.1021/cr00044a004 pmid: 28686460 |
|
(e) Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
doi: 10.1246/bcsj.55.909 pmid: 28686460 |
|
(f) Russell, G. A.; Yao, C. F. J. Org. Chem. 1992, 57, 6508.
doi: 10.1021/jo00050a026 pmid: 28686460 |
|
(g) Zhong, P.; Huang, X.; Xiong, Z. X. Synlett 1999, 721.
pmid: 28686460 |
|
(h) Zhong, P.; Xiong, Z. X.; Huang, X. Synth. Commun. 2000, 30, 273.
doi: 10.1080/00397910008087318 pmid: 28686460 |
|
(i) Kabalka, G. K.; Guchhait, S. K. Org. Lett. 2003, 5, 729.
pmid: 28686460 |
|
(j) Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681.
pmid: 28686460 |
|
(k) Zhuang, R. Q.; Xu, J.; Cai, Z. S.; Tang, G.; Fang, M. J.; Zhao, Y. F. Org. Lett. 2011, 13, 2110.
doi: 10.1021/ol200465z pmid: 28686460 |
|
(l) Evano, G.; Tadiparthi, K.; Couty, F. Chem. Commun. 2011, 47, 179.
doi: 10.1039/C0CC01617A pmid: 28686460 |
|
(m) Liu, L.; wang, Y. L.; Zeng, Z. P.; Xu, P. X.; Gao, Y. X.; Yin, Y. W.; Zhao, Y. F. Adv. Synth. Catal. 2013, 355, 659.
doi: 10.1002/adsc.201200853 pmid: 28686460 |
|
(n) Wu, Y. L.; Liu, L. L.; Yan, K. L.; Xu, P. X.; Gao, Y. X.; Zhao, Y. F. J. Org. Chem. 2014, 79, 8118.
doi: 10.1021/jo501321m pmid: 28686460 |
|
(o) Liu, L.; Lv, Y.; Wu, Y. L.; gao, X.; Zeng, Z. P.; Gao, Y. X.; Tang, G.; Zhao, Y. F. RSC Adv. 2014, 4, 2322.
doi: 10.1039/C3RA45212C pmid: 28686460 |
|
(p) Gui, Q. W.; Hu, L.; Chen, X.; Liu, J. D.; Tan, Z. Chem. Commun. 2015, 51, 13922.
doi: 10.1039/C5CC04826E pmid: 28686460 |
|
(q) Xue, J. F.; Zhou, S. F.; Liu, Y. Y.; Pan, X. Q.; Zou, J. P.; Asekun, O. T. Org. Biomol. Chem. 2015, 13, 4896.
doi: 10.1039/C5OB00404G pmid: 28686460 |
|
(r) Yuan, J. W.; Yang, L. R.; Mao, P.; Qu, L. B. RSC Adv. 2016, 6, 87058.
doi: 10.1039/C6RA19002B pmid: 28686460 |
|
(s) Liaom, L. L.; Gui, Y. Y.; Zhang, X. B.; Shen, G.; Liu, H. D.; Zhou, W. J.; Li, J.; Yu, D. G. Org. Lett. 2017, 19, 3735.
doi: 10.1021/acs.orglett.7b01561 pmid: 28686460 |
|
(t) Gu, J.; Cai, C. Org. Biomol. Chem. 2017, 15, 4226.
doi: 10.1039/C7OB00505A pmid: 28686460 |
|
(u) Liu, L. X.; Zhou, D.; Dong, J. Y.; Zhou, Y. B.; Yin, S. F.; Han, L. B. J. Org. Chem. 2018, 83, 4190.
doi: 10.1021/acs.joc.8b00187 pmid: 28686460 |
|
(v) Wang, L.; Yang, Z.; Zhu, H. J.; Liu, H. T.; Lv, S. P.; Xu, Y. Eur. J. Org. Chem. 2019, 2019, 2138.
doi: 10.1002/ejoc.201801678 pmid: 28686460 |
|
(w) Ghasemzadeh, M. S.; Akhlaghinia, B. New J. Chem. 2019, 43, 5341.
doi: 10.1039/c9nj00352e pmid: 28686460 |
|
(x) Liu, C. W.; Ji, C. L.; Zhou, T. L.; Hong, X.; Szostak, M. Org. Lett. 2019, 21, 9256.
doi: 10.1021/acs.orglett.9b03678 pmid: 28686460 |
|
(y) Qiao, B. K.; Cao, H. Q.; Huang, Y. J.; Zhang, Y.; Nie, J.; Zhang, F. G.; Ma, J. A. Chin. J. Chem. 2018, 36, 809.
doi: 10.1002/cjoc.v36.9 pmid: 28686460 |
|
(z) Ren, L. J.; Ran, M. G.; Fang, X. H.; Zhao, L.; Yao, Q. L. Chin. J. Org. Chem. 2018, 38, 2791. (in Chinese)
doi: 10.6023/cjoc201803016 pmid: 28686460 |
|
(任林静, 冉茂刚, 方学红, 赵玲, 姚秋丽, 有机化学, 2018, 38, 2791.)
doi: 10.6023/cjoc201803016 pmid: 28686460 |
|
[3] |
(a) Han, L. B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
doi: 10.1021/ja953690t |
(b) Han, L. B.; Hua, R. M.; Tanaka, M. Angew. Chem. Int. Ed. 1998, 37, 94.
|
|
(c) Lai, C. B.; Xi, C. J.; Chen, C.; Ma, M. M.; Hong, X. Y. Chem. Commun. 2003, 2736.
|
|
(d) Trostyanskaya, I. G.; Beletskaya, I. P. Tetrahedron 2005, 61, 6315.
doi: 10.1016/j.tet.2005.03.107 |
|
(e) Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P. Russ. J. Org. Chem. 2010, 46, 1269.
doi: 10.1134/S1070428010090010 |
|
(f) Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P.; Starikova, Z. A. Adv. Synth. Catal. 2010, 352, 2979.
doi: 10.1002/adsc.v352.17 |
|
(g) Xu, Q.; Shen, R. W.; Ono, Y.; Nagahata, R.; Shimada, S.; Goto, M.; Han, L. B. Chem. Commun. 2011, 47, 2333.
doi: 10.1039/C0CC03436C |
|
(h) Khemchyan, L. L.; Ivanova, J. V.; Zalesskiy, S. S.; Ananikov, V. P.; Beletskaya, I. P.; Starikova, Z. A. Adv. Synth. Catal. 2014, 356, 771.
doi: 10.1002/adsc.v356.4 |
|
(i) Islas, R. E.; García, J. J. ChemCatChem 2017, 9, 4125.
doi: 10.1002/cctc.v9.21 |
|
(j) Chen, T. Q.; Zhao, C. Q.; Han, L. B. J. Am. Chem. Soc. 2018, 140, 3139.
doi: 10.1021/jacs.8b00550 |
|
(k) Wei, X. H.; Bai, C. Y.; Zhao, L. B.; Zhang, P.; Li, Z. H.; Wang, Y. B.; Su, Q. Chin. J. Chem. 2021, 39, 1855.
doi: 10.1002/cjoc.v39.7 |
|
[4] |
Kers, A.; Kers, I.; Stawinski, J.; Sobkowski, M.; Kraszewski, A. Synthesis 1995, 427.
|
[5] |
(a) Huang, H.; Denne, J.; Yang, C. H.; Wang, H. B.; Kang, J. Y. Angew. Chem. Int. Ed. 2018, 57, 6624.
doi: 10.1002/anie.v57.22 |
(b) Adler, P.; Pons, A.; Li, J.; Heider, J.; Brutiu, B. R.; Maulide, N. Angew. Chem. Int. Ed. 2018, 57, 13330.
doi: 10.1002/anie.v57.40 |
|
[6] |
(a) Xu, K.; Hu, H.; Yang, F.; Wu, Y. J. Eur. J. Org. Chem. 2013, 2013, 319.
|
(b) Xu, K.; Yang, F.; Zhang, G. D.; Wu, Y. J. Green Chem. 2013, 15, 1055.
doi: 10.1039/c3gc00030c |
|
[7] |
Ouyang, K. B.; Xi, Z. F. Acta Chim. Sinica 2013, 71, 13.
doi: 10.6023/A12110984 |
[8] |
Park, K.; Bae, G.; Moon, J.; Choe, J.; Song, K.; Lee, S. J. Org. Chem. 2010, 75, 6244
doi: 10.1021/jo101398a |
[9] |
Kobayashi, Y.; William, A. D. Adv. Synth. Catal. 2004, 346, 1749.
doi: 10.1002/adsc.200404191 |
[1] | Hao Qin, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, Xiangping Hu. Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 282-290. |
[2] | Xianqiang Meng, Yi Yang, Wanjie Liang, Jingtao Wang, Rongkui Zhang, Hui Liu. Palladium-Catalyzed Regioselective Aryl Phenoxylation of Allenamide [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 224-231. |
[3] | Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225. |
[4] | Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF3•OEt2 in Organic Synthesis as a Catalyst or Synthon [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118. |
[5] | Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088. |
[6] | Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960. |
[7] | Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627. |
[8] | Min Lü, Aimei Yang, Yu Zhang, Jianting Sun, Bangguo Wei. Fe(OTf)3-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1777-1785. |
[9] | Deliang Kong, Wen Dai, Yiling Zhao, Yilin Chen, Hongping Zhu. Study on Oxidative Cycloaddition Reactions of Amidinatoboryl-aminosilylenes toward Ketone and Diketone Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1843-1851. |
[10] | Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044. |
[11] | Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959. |
[12] | Junxiu Liang, Yazhou Liu, Amu Wang, Yanchao Wu, Xiaofeng Ma, Huijing Li. Dearomatization of Halonaphthols via an Intermolecular [4+1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3888-3899. |
[13] | Wei Xiong, Bin Shi, Xuan Jiang, Liangqiu Lu, Wenjing Xiao. Ligand-Switched Pd-Catalyzed Divergent Transformations of Vinyl Cyclic Carbamates and Isocyanates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 265-273. |
[14] | Junjiao Wang, Yuyu Lv, Yongwei Shang, Zhenli Cui, Ke-Hu Wang, Danfeng Huang, Yulai Hu. Research Progress of Reactions Participated by α-Hydroxy Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2300-2321. |
[15] | Haoru Song, Jianting Sun, Min LÜ, Yiwen Liu, Bangguo Wei. Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2433-2437. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||