有机化学 ›› 2021, Vol. 41 ›› Issue (6): 2290-2301.DOI: 10.6023/cjoc202102051 上一篇 下一篇
研究论文
刘宇a,b, 陈赞a, 陈镤a, 熊碧权a, 谢军a,*(), 刘岸a,*(), 梁云b, 唐课文a
收稿日期:
2021-02-27
修回日期:
2021-03-18
发布日期:
2021-03-25
通讯作者:
谢军, 刘岸
基金资助:
Yu Liua,b, Zan Chena, Pu Chena, Biquan Xionga, Jun Xiea(), An Liua(), Yun Liangb, Kewen Tanga
Received:
2021-02-27
Revised:
2021-03-18
Published:
2021-03-25
Contact:
Jun Xie, An Liu
Supported by:
文章分享
报道了一种在无过渡金属条件下可见光催化炔烃与环酮肟衍生物的串联氰基烷基磺酰化/环化反应, 通过SO2的插入合成2-氰基烷基磺酰基-9H-吡咯并[1,2-a]吲哚. 该碳碳叁键的双官能团化包括自由基机理, 依次经历了亚胺自由基的形成、环酮的开环、SO2的插入、磺酰基对碳碳叁键的加成、分子内环化和异构化.
刘宇, 陈赞, 陈镤, 熊碧权, 谢军, 刘岸, 梁云, 唐课文. 可见光催化炔烃串联氰基烷基磺酰化/环化[J]. 有机化学, 2021, 41(6): 2290-2301.
Yu Liu, Zan Chen, Pu Chen, Biquan Xiong, Jun Xie, An Liu, Yun Liang, Kewen Tang. Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2290-2301.
Entry | Variation from the standard conditions | Yield/% |
---|---|---|
1 | None | 81 |
2 | 2a-1 instead of 2a | 13 |
3 | 2a-2 instead of 2a | 25 |
4 | 2a-3 instead of 2a | 46 |
5 | 2a-4 instead of 2a | 55 |
6 | 2a-5 instead of 2a | 51 |
7 | 2a-6 instead of 2a | 50 |
8 | DABSO instead of K2S2O5 | 8 |
9 | Thiourea dioxide instead of K2S2O5 | 67 |
10c | Na2S2O5 instead of K2S2O5 | 73 |
11c | Without Na2-Eosin Y | 0 |
12 | Ir(ppy)3 instead of Na2-Eosin Y | 59 |
13 | Ru(bpy)3Cl2 instead of Na2-Eosin Y | 34 |
14 | Eosin Y instead of Na2-Eosin Y | 64 |
15 | Without additional light | 0 |
16 | Na2-Eosin Y (5 mol%) | 81 |
17 | Toluene instead of CH3CN | 40 |
18 | THF instead of CH3CN | 38 |
19c | DMF instead of CH3CN | 27 |
20c | Dioxane instead of CH3CN | 44 |
21 | DMSO instead of CH3CN | 32 |
22 | 3 W blue LED light | 61 |
23 | 12 W blue LED light | 54 |
24 | 36 W compact fluorescent light | 45 |
25 | At 100 ℃ | 70 |
26 | At 60 ℃ | 42 |
27 | For 32 h | 80 |
28d | None | 52 |
Entry | Variation from the standard conditions | Yield/% |
---|---|---|
1 | None | 81 |
2 | 2a-1 instead of 2a | 13 |
3 | 2a-2 instead of 2a | 25 |
4 | 2a-3 instead of 2a | 46 |
5 | 2a-4 instead of 2a | 55 |
6 | 2a-5 instead of 2a | 51 |
7 | 2a-6 instead of 2a | 50 |
8 | DABSO instead of K2S2O5 | 8 |
9 | Thiourea dioxide instead of K2S2O5 | 67 |
10c | Na2S2O5 instead of K2S2O5 | 73 |
11c | Without Na2-Eosin Y | 0 |
12 | Ir(ppy)3 instead of Na2-Eosin Y | 59 |
13 | Ru(bpy)3Cl2 instead of Na2-Eosin Y | 34 |
14 | Eosin Y instead of Na2-Eosin Y | 64 |
15 | Without additional light | 0 |
16 | Na2-Eosin Y (5 mol%) | 81 |
17 | Toluene instead of CH3CN | 40 |
18 | THF instead of CH3CN | 38 |
19c | DMF instead of CH3CN | 27 |
20c | Dioxane instead of CH3CN | 44 |
21 | DMSO instead of CH3CN | 32 |
22 | 3 W blue LED light | 61 |
23 | 12 W blue LED light | 54 |
24 | 36 W compact fluorescent light | 45 |
25 | At 100 ℃ | 70 |
26 | At 60 ℃ | 42 |
27 | For 32 h | 80 |
28d | None | 52 |
[1] |
(a) Wang, T.; Jiao, N. Acc. Chem. Res. 2014, 47,1137.
|
(b) Hu, P.; Chai, J.-C.; Duan, Y.-L.; Liu, Z.-H.; Cui, G.-L.; Chen, L.-Q. J. Mater. Chem. A 2016, 4,10070.
|
|
(c) Bagal, D.-B.; Bhanage, B.-M. Adv. Synth. Catal. 2015, 357,883.
|
|
(d) Yan, G.; Zhang, Y.; Wang, J. Adv. Synth. Catal. 2017, 359,4068.
|
|
(e) Fleming, F.-F.; Yao, L.-H.; Ravikumar, P.-C.; Funk, L.; Shook, B.-C. J. Med. Chem. 2010, 53,7902.
|
|
(f) Rappoport, Z. The Chemistry of the Cyano Group, Wiley, London, 1970, pp.121~312.
|
|
(g) Fleming, F.-F. Nat. Prod. Rep. 1999, 16,597.
|
|
(h) Fatiadi, A. J. In Preparation and Synthetic Applications of Cyano Compounds, Eds.: Patai, S.; Rappoport, Z., Wiley-VCH, New York, 1983.
|
|
[2] |
(a) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7,3757.
|
(b) Wang, G.-W.; Zhou, A.-X.; Wang, J.-J.; Hu, R.-B.; Yang, S.-D. Org. Lett. 2013, 15,5270.
|
|
(c) Shen, J.-X.; Yang, D.-J.; Liu, Y.-X.; Qin, S.-S.; Zhang, J.-W.; Sun, J.-K.; Liu, C.-H.; Liu, C.-Y.; Zhao, X.-M.; Chu, C.-H.; Liu, R.-H. Org. Lett. 2014, 16,350.
|
|
(d) Takaya, H.; Ito, M.; Murahashi, S.-I. J. Am. Chem. Soc. 2009, 131,10824.
|
|
(e) Li, Y.; Liu, B.; Li, H.-B.; Wang, Q.; Li, J.-H. Chem. Commun. 2015, 51,1024.
|
|
(f) Cheng, P.; Wang, W.; Wang, L.; Zeng, J.-G.; Reiser, O.; Liang, Y. Tetrahedron Lett. 2019, 60,1408.
|
|
[3] |
(a) Kumagai, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126,13632.
|
(b) Zhang, J.-L.; Liu, Y.; Song, R.-J.; Jiang, G.-F.; Li, J.-H. Synlett 2014, 25,1031.
|
|
(c) Chakraborty, S.; Patel, Y.-J.; Krause, J.-A.; Guan, H. Angew. Chem., Int. Ed. 2013, 52,7523.
|
|
(d) Pan, C.-D.; Zhang, H.-L.; Zhu, C.-J. Org. Biomol. Chem. 2015, 13,361.
|
|
(e) Hu, M.; Zou, H.-X.; Song, R.-J.; Xiang, J.-N.; Li, J.-H. Org. Lett. 2016, 18,6460.
|
|
(f) Evans, M.-E.; Li, T.; Jones, W.-D. J. Am. Chem. Soc. 2010, 132,16278.
|
|
(g) Chen, Z.; Zhou, Q.; Chen, Q.-N.; Chen, P.; Xiong, B.-Q.; Liang, Y.; Tang, K.-W.; Xie, J.; Liu, Y. Org. Biomol. Chem. 2020, 18,8677.
|
|
[4] |
(a) Wu, T.; Mu, X.; Liu, G.-S. Angew. Chem., Int. Ed. 2011, 50,12578.
|
(b) Li, X.-Q.; Xu, J.; Gao, Y.-Z.; Fang, H.; Tang, G.; Zhao, Y.-F. J. Org. Chem. 2015, 80,2621.
|
|
(c) Liu, Y.-B.; Yang, K.; Ge, H.-B. Chem. Sci. 2016, 7,2804.
|
|
(d) Chatalova-Sazepin, C.; Wang, Q.; Sammis, G.-M.; Zhu, J. Angew. Chem., Int. Ed. 2015, 54,5443.
|
|
(e) Bunescu, A.; Wang, Q.; Zhu, J.-P. Org. Lett. 2015, 17,1890.
|
|
(f) Bunescu, A.; Ha, T.-M.; Wang, Q.; Zhu, J.-P. Angew. Chem., Int. Ed. 2017, 56,10555.
|
|
(g) Liu, Y.-Y.; Yang, X.-H.; Song, R.-J.; Luo, S.-L.; Li, J.-H. Nat. Commun. 2017, 8,14720.
|
|
[5] |
(a) Boivin, J.; Fouquet, E.; Zard, S.-Z.; J. Am. Chem. Soc. 1991, 113,1055.
|
(b) Nishimura, T.; Yoshinaka, T.; Nishiguchi, Y.; Maeda, Y.; Uemura, S. Org. Lett. 2005, 7,2425.
|
|
(c) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122,12049.
|
|
(d) Yang, H.-B.; Selander, N. Chem.-Eur. J. 2017, 23,1779.
|
|
(e) Yang, H.-B.; Pathipati, S.-R.; Selander, N. ACS Catal. 2017, 7,8441.
|
|
(f) Morcillo, S.-P. Angew. Chem., Int. Ed. 2019, 58,14044.
|
|
(g) Xiao, T.; Huang, H.; An, D.; Zhou, L. Synthesis 2020, 52,1585.
|
|
Song, C.-H.; Shen, X. Yu, F. He, Y.-P.; Yu, S.-Y. Chin. J. Org. Chem. 2020, 40,3748(in Chinese).
|
|
(宋常华, 沈许, 于芳, 何宇鹏, 俞寿云, 有机化学, 2020, 40,3748.)
|
|
[6] |
(a) Yu, X.-Y.; Zhao, Q.-Q.; Chen, J.; Chen, J.-P.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57,15505.
|
(b) Yu, X.-Y.; Wang, P.-Z.; Yan, D.-M.; Liu, B.; Chen, J.-R.; Xiao, W.-J. Adv. Synth. Catal. 2018, 360,3601.
|
|
(c) He, B.-Q.; Yu, X.-Y.; Wang, P.-Z.; Chen, J.-R.; Xiao, W.-J. Chem. Commun. 2018, 54,12262.
|
|
(d) Lu, B.; Cheng, Y.; Chen, L.-Y.; Chen, J.-R.; Xiao, W.-J. ACS. Catal. 2019, 9,8159.
|
|
(e) Yu, X.-Y.; Chen, J.-R.; Wang, P.-Z.; Yang, M.-N.; Liang, D.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57,738.
|
|
(f) Xiao, W.; Xiao, W.-J. Chin. Chem. Lett. 2020, 31,3083.
|
|
(g) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121,506.
|
|
[7] |
(a) Tang, Y.-Q.; Yang, J.-C.; Wang, L.; Fan, M.-J.; Guo, L.-N. Org. Lett. 2019, 21,5178.
|
(b) Wu, J.; Zhang, J.-Y.; Gao, P.; Xu, S.-L.; Guo, L.-N. J. Org. Chem. 2018, 83,1046.
|
|
(c) Zhang, J.-J.; Duan, X.-H.; Wu, Y.; Yang, J.-C. Guo, L.-N. Chem. Sci. 2019, 10,161.
|
|
(d) Yang, L.; Gao, P.; Duan, X.-H.; Gu, Y.-R.; Guo, L.-N. Org. Lett. 2018, 20,1034.
|
|
(e) He, Y.; Lou, J.; Wu, K.-K.; Wang, H.-M.; Yu, Z.-K. J. Org. Chem. 2019, 84,2178.
|
|
(f) Yin, Z.-P.; Rabeah, J.; Brückner, A.; Wu, X.-F. ACS Catal. 2018, 8,10926.
|
|
(g) Yu, J.-X.; Teng, F.; Xiang, J.-N.; Deng, W.; Li, J.-H. Org. Lett. 2019, 21,9434.
|
|
(h) Zhou, X.-S.; Cheng, Y.; Chen, J.; Yu, X.-Y.; Xiao, W.-J.; Chen, J.-R. ChemCatChem 2019, 11,5300.
|
|
[8] |
(a) Chen, Z.; Zhou, Q.; Wang, Q.-L.; Chen, P.; Xiong, B.-Q.; Liang, Y.; Tang, K.-W.; Liu, Y. Adv. Synth. Catal. 2020, 362,3004.
|
(b) Zhang, J.; Zhang, X.-F.; Xie, W.-L.; Ye, S.-Q.; Wu, J. Org. Lett. 2019, 21,4950.
|
|
(c) Liu, Y.; Wang, Q.-L.; Chen, Z.; Li, H.; Xiong, B.-Q.; Zhang, P.-L.; Tang, K.-W. Chem. Commun. 2020, 56,3011.
|
|
(d) Zheng, M.; Li, G.-G.; Lu, H.-J. Org. Lett. 2019, 21,1216.
|
|
(e) Yin, Z.-P.; Rabeah, J.; Brückner, A.; Wu, X.-F. Org. Lett. 2019, 21,1766.
|
|
(f) Lou, J.; He, Y.; Li, Y.-L.; Yu, Z.-K. Adv. Synth. Catal. 2019, 361,3787.
|
|
(g) Shen, X.; Zhao, J.-J.; Yu, S.-Y. Org. Lett. 2018, 20,5523.
|
|
(h) Tian, L.; Guo, S.-Q.; Wang, R.; Li, Y.; Tang, C.-L.; Shi, L.-L.; Fu, J.-K. Chem. Commun. 2019, 55,5347.
|
|
(i) Zhao, B.-L.; Shi, Z.-Z. Angew. Chem., Int. Ed. 2017, 56,12727.
|
|
(j) Li, L.-Y.; Chen, H.-G.; Mei, M.-J.; Zhou, L. Chem. Commun. 2017, 53,11544.
|
|
(k) Xiao, W.; Wu, J. Chin. Chem. Lett. 2020, 31,3083.
|
|
(l) Min, Q.-Q.; Li, N.; Chen, G.-L.; Liu, F. Org. Chem. Front. 2019, 6,1200.
|
|
[9] |
(a) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45,2044.
|
(b) Xiong, T.; Zhang, Q. Chem. Soc. Rev. 2016, 45,3069.
|
|
(c) Wang, P.-Z.; Zhao, Q.-Q.; Xiao, W.-J.; Chen, J.-R. Green Synth. Catal. 2020, 1,42.
|
|
(d) Jiang, H.; Studer, A. CCS Chem. 2019, 1,38.
|
|
[10] |
(a) Shaaban, S.; Liang, S.; Liu, N.-W.; Manolikakes, G. Org. Biomol. Chem. 2017, 15,1947.
|
(b) Rayner, C.-M. Contemp. Org. Synth. 1994, 1,191.
|
|
(c) Meadows, D.-C.; Gervay-Hague, J. Med. Res. Rev. 2006, 26,793.
|
|
(d) Markitanov, Y.-M.; Timoshenko, V.-M.; Shenko, Y.-G. J. Sulfur Chem. 2014, 35,188.
|
|
(e) Fukuda, H.; Frank, F.-J.; Truce, W.-E. J. Org. Chem. 1963, 28,1420.
|
|
(f) Fang, Y.-Y.; Luo, Z.-G.; Xu, X.-M. RSC Adv. 2016, 6,59661.
|
|
(g) Alba, A.-N.-R.; Companyóa, X.; Rios, R. Chem. Soc. Rev. 2010, 39,2018.
|
|
[11] |
(a) Rao, W.-H.; Zhan, B.-B.; Chen, K.; Ling, P.-X.; Zhang, Z.-Z.; Shi, B.-F. Org. Lett. 2015, 17,3552.
|
(b) Cabrera Afonso, M.-J.; Lu, Z.-P.; Kelly, C.-B.; Lang, S.-B.; Dykstra, R.; Gutierrez, O.; Molander, G.-A. Chem. Sci. 2018, 9,3186.
|
|
(c) Song, R.-J.; Liu, Y.; Liu, Y.-Y.; Li, J.-H. J. Org. Chem. 2011, 76,1001.
|
|
(d) Xie, L.-Y.; Peng, S.; Liu, F.; Chen, G.-R.; Xia, W.; Yu, X.-Y.; Li, W.-F.; Cao, Z.; He, W.-M. Org. Chem. Front. 2018, 5,2604.
|
|
(e) Xiao, F.-H.; Liu, C.; Yuan, S.-S.; Huang, H.-W.; Deng, G.-J. J. Org. Chem. 2018, 83,10420.
|
|
(f) Howell, B.-A.; Daniel, Y.-G. J. Fire Sci. 2018, 36,518.
|
|
[12] |
(a) Zheng, D.; Wu, J. Sulfur Dioxide Insertion Reactions for Organic Synthesis, Nature Springer, Berlin, 2017.
|
(b) Liu, J.-D.; Zheng, L.-Y. Adv. Synth. Catal. 2019, 361,1710.
|
|
(c) Ye, S.-Q.; Qiu, G.-Y.-S.; Wu, J. Chem. Commun. 2019, 55,1013.
|
|
(d) Qiu, G.-Y.-S.; Lai, L.-F.; Cheng, J.; Wu, J. Chem. Commun. 2018, 54,10405.
|
|
(e) Qiu, G.-Y.-S.; Zhou, K.-D.; Gao, L.; Wu, J. Org. Chem. Front. 2018, 5,691.
|
|
(f) Zhu, J.; Yang, W.-C.; Wang, X.-D.; Wu, L. Adv. Synth. Catal. 2018, 360,386.
|
|
(g) Liu, G.; Fan, C.-B.; Wu, J. Org. Biomol. Chem. 2015, 13,1592.
|
|
(h) Ye, S.-Q.; Zhou, K.-D.; Rojsitthisak, P.; Wu, J. Org. Chem. Front. 2020, 7,14.
|
|
[13] |
(a) Wu, Y.-C.; Jiang, S.-S.; Luo, S.-Z.; Song, R.-J.; Li, J.-H. Chem. Commun. 2019, 55,8995.
|
(b) Yang, J.; Liu, Y.-Y.; Song, R.-J.; Peng, Z.-H.; Li, J.-H. Adv. Synth. Catal. 2016, 358,2286.
|
|
(c) Gong, X.-X.; Wang, M.-J.; Ye, S.-Q.; Wu, J. Org. Lett. 2019, 21,1156.
|
|
(d) An, Y.-Y.; Wu, J. Org. Lett. 2017, 19,6028.
|
|
(e) Rostami, A.; Akradi, J. Tetrahedron Lett. 2010, 51,3501.
|
|
(f) Rahimizadeha, M., Rajabzadehb, G., Hossein, S.-M., AliShiri, E. J. Mol. Catal. A 2010, 323,59.
|
|
(g) Su, W.-G. Tetrahedron Lett. 1994, 35,4955.
|
|
(h) Liu, Q.-S.; Lv, Y.-F.; Liu, R.-S.; Zhao, X.-H.; Wang, J.-W.; Wei, W. Chin. Chem. Lett. 2021, 32,136.
|
|
(i) He, F.-S.; Yang, M.; Ye, S.-Q.; Wu, J. Chin. Chem. Lett. 2021, 32,461.
|
|
[14] |
(a) Liu, T.; Zheng, D.-Q.; Li, Z.-H.; Wu, J. Adv. Synth. Catal. 2018, 360,865.
|
(b) Chen, H.-J.; Liu, M.-L.; Qiu, G.-Y.-S.; Wu, J. Adv. Synth. Catal. 2019, 361,146.
|
|
(c) Li, Y.-W.; Mao, R.-Y.; Wu, J. Org. Lett. 2017, 19,4472.
|
|
(d) Woolven, H.; González-Rodríguez, C.; Marco, I.; Thompson, A.-L.; Willis, M.-C. Org. Lett. 2011, 13,4876.
|
|
(e) Vedovato, V.; Talbot, E.-P.-A.; Willis, M.-C. Org. Lett. 2018, 20,5493.
|
|
(f) Wang, Y.; Deng, L.-L.; Zhou, J.; Wang, X.-C.; Mei, H.-B.; Han, J.-L.; Pan, Y. Adv. Synth. Catal. 2018, 360,1060.
|
|
(g) Liu, T.; Zhou, W.; Wu, J. Org. Lett. 2017, 19,6638.
|
|
(h) Deeming, A.-S.; Russell, C.-J.; Willis, M.-C. Angew. Chem., Int. Ed. 2016, 55,747.
|
|
(i) Sun, K.; Shi, Z.; Liu, Z.; Luan, B.; Zhu, J. Org. Lett. 2018, 20,6687.
|
|
(j) Zhou, K.-D.; Chen, J.-Q.; Wu, J. Chin. Chem. Lett. 2020, 31,2996.
|
|
[15] |
(a) Wang, M.; Chen, S.-H.; Jiang, X.-F. Org. Lett. 2017, 19,4916.
|
(b) Gong, X.-X.; Li, X.-F.; Xie, W.-L.; Wu, J.; Ye, S.-Q. Org. Chem. Front. 2019, 6,1863.
|
|
[16] |
(a) Kumar, S.; Verma, S.; Jain, S.-L.; Sain, B. Tetrahedron Lett. 2011, 52,3393.
|
(b) Ye, S.-Q.; Li, Y.-W.; Wu, J.; Li, Z.-M. Chem. Commun. 2019, 55,2489.
|
|
(c) Chen, S.-H.; Li, Y.-P.; Wang, M.; Jiang, X.-F. Green Chem. 2020, 22,322.
|
|
(d) Li, Y.-W.; Liu, T.; Qiu, G.-Y.-S.; Wu, J. Adv. Synth. Catal. 2019, 361,1154.
|
|
(e) Gong, X.-X.; Chen, J.-H.; Lai, L.-F.; Cheng, J.; Sun, J.-T.; Wu, J. Chem. Commun. 2018, 54,11172.
|
|
[17] |
(a) Liu, Y.; Chen, Z.; Wang, Q.-L.; Chen, P.; Xie, J.; Xiong, B.-Q.; Zhang, P.-L.; Tang, K.-W. J. Org. Chem. 2020, 85,2385.
|
(b) Xie, X.-Y.; Li, P.-H.; Wang, L. Eur. J. Org. Chem. 2019,221.
|
|
(c) Liu, Y.; Wang, Q.-L.; Chen, Z.; Chen, P.; Tang, K.-W.; Zhou, Q.; Xie, J. Org. Biomol. Chem. 2019, 17,10020.
|
|
(d) Zhu, J.-W.; Sun, S.; Xia, M.-F.; Gu, N.; Cheng, J. Org. Chem. Front. 2017, 4,2153.
|
|
(e) Zhu, X.-Y.; Li, M.; Han, Y.-P.; Chen, S.; Li, X.-S.; Liang, Y.-M. J. Org. Chem. 2017, 82,8761.
|
|
(f) Xie, X.-Y.; Li, P.-H.; Wang, L. Eur. J. Org. Chem. 2019,221.
|
|
(g) Zhang, P.-B.; Shi, S.-S.; Gao, X.; Han, S.; Lin, J.-M.; Zhao, Y.-F. Org. Biomol. Chem. 2019, 17,2873.
|
|
(h) Zhang, H.-L.; Li, W.-P.; Zhu, C.-J. J. Org. Chem. 2017, 82,2199.
|
|
(i) Chen, S.; Zhang, P.-B.; Shu, W.-Y.; Gao, Y.-Z.; Tang, G.; Zhao, Y.-F. Org. Lett. 2016, 18,5712.
|
|
[18] |
(a) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51,6828.
|
(b) Ouyang, X.-H.; Cheng, J.; Li, J.-H. Chem. Commun. 2018, 54,8745.
|
|
(c) Hari, D. P.; König, B. Angew. Chem., Int. Ed. 2013, 52,4734.
|
|
(d) Hari, D. P.; Schroll, P.; König, B. J. Am. Chem. Soc. 2012, 134,2958.
|
|
(e) Ding, W.; Lu, L.-Q.; Zhou, Q.-Q.; Wei, Y.; Chen, J.-R.; Xiao, W.-J. J. Am. Chem. Soc. 2017, 139,63.
|
|
(f) Zhang, M.; Li, N.; Tao, X.-Y.; Ruzi, R.; Yu, S.-Y.; Zhu, C.-J. Chem. Commun. 2017, 53,10228.
|
|
(g) Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50,6164.
|
|
(h) Liu, R.-S.; Liu, Q.-S.; Meng, H.-R.; Ding, H.-Y.; Hao, J.-D.; Ji, Z.-Y.; Yue, H.-L.; Wei, W. Org. Chem. Front. 2021, 8,1970.
|
|
[19] |
(a) Yong, X.; Han, Y.-F.; Li, Y.; Song, R.-J.; Li, J.-H. Chem. Commun. 2018, 54,12816.
|
(b) Qin, Q.; Ren, D.; Yu, S. Org. Biomol. Chem. 2015, 13,10295.
|
|
(c) Sun, X.; Yu, S. Chem. Commun. 2016, 52,10898.
|
|
(d) Ouyang, X.-H.; Li, Y.; Song, R.-J.; Li, J.-H. Org. Lett. 2018, 20,6659.
|
|
(e) Han, Y.-Y.; Wang, H.; Yu, S. Org. Chem. Front. 2016, 3,953.
|
|
(f) Sun, J.; He, Y.; An, X.-D.; Zhang, X.; Yu, L.; Yu, S. Org. Chem. Front. 2018, 5,977.
|
|
[20] |
(a) Li, Y.; Mou, T.; Lu, L.; Jiang, X. Chem. Commun. 2019, 55,14299.
|
(b) Zhou, H.; Deng, X.; Ma, Z.; Zhang, A.; Qin, Q.; Tan, R.-X.; Yu, S. Org. Biomol. Chem. 2016, 14,6065.
|
|
(c) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49,1911.
|
|
(d) Li, M.; Yang, J.; Ouyang, X.-H.; Yang, Y.; Hu, M.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2016, 81,7148.
|
|
(e) Liu, Y.; Wang, Q.-L.; Chen, Z.; Zhou, Q.; Xiong, B.-Q.; Zhang, P.-L.; Tang, K.-W. Chem. Commun. 2019, 55,12212.
|
|
(f) Wang, P.-Z.; Gao, Y.; Chen, J.; Huan, X.-D.; Xiao, W.-J.; Chen, J.-R. ChemRxiv doi: 10. 26434/chemrxiv.13325669.v1.
|
|
[21] |
(a) Yan, D.-M.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58,378.
|
(b) Yan, J.-M.; Cheo, H.-W.; Teo, W. K.; Shi, X. C.; Wu, H.; Idres, S.-B.; Deng, L.-W.; Wu, J. J. Am. Chem. Soc. 2020, 142,11357.
|
|
(c) Huang, B.-B.; Zhao, Y.-T.; Yang, C.; Gao, Y.; Xia, W.-J. Org. Lett. 2017, 19,3799.
|
|
(d) Xuan, J.; Feng, Z.-J.; Duan, S.-W.; Xiao, W.-J. RSC Adv. 2012, 2,4065.
|
|
(e) Zhang, J.; Wang, L.; Liu, Q.; Yang, Z.; Huang, Y. Chem. Commun. 2013, 49,11662.
|
|
(f) Liu, Y.; Wang, Q.-L.; Xiong, B.-Q.; Zhang, P.-L.; Yang, C.-A.; Gong, Y.-X.; Liao, J.; Zhou, Q. Synlett 2018, 29,2396.
|
[1] | 朱彦硕, 王红言, 舒朋华, 张克娜, 王琪琳. 烷氧自由基引发1,5-氢原子转移实现C(sp3)—H键官能团化的研究进展[J]. 有机化学, 2024, 44(1): 1-17. |
[2] | 童红恩, 郭宏宇, 周荣. 可见光促进惰性碳-氢键对羰基的加成反应进展[J]. 有机化学, 2024, 44(1): 54-69. |
[3] | 杨晓娜, 郭宏宇, 周荣. 可见光促进有机硅化合物参与的化学转化[J]. 有机化学, 2023, 43(8): 2720-2742. |
[4] | 高艳华, 张银潘, 张妍, 宋涛, 杨勇. 可见光驱动表面富含氧空位Nb2O5催化醇氧化反应[J]. 有机化学, 2023, 43(7): 2572-2579. |
[5] | 赵金晓, 魏彤辉, 柯森, 李毅. 可见光催化合成二氟烷基取代的多环吲哚化合物[J]. 有机化学, 2023, 43(3): 1102-1114. |
[6] | 赵瑜, 段玉荣, 史时辉, 白育斌, 黄亮珠, 杨晓军, 张琰图, 冯彬, 张建波, 张秋禹. 可见光促进高价碘(III)试剂参与反应的研究进展[J]. 有机化学, 2023, 43(12): 4106-4140. |
[7] | 吴宇恒, 颜岩, 寮渭巍. 双功能二氧化硫替代物在合成磺酰类化合物中的研究进展[J]. 有机化学, 2023, 43(11): 3713-3727. |
[8] | 陈凤娟, 刘罗, 张子露, 曾伟. 可见光催化有机硅的合成研究进展[J]. 有机化学, 2023, 43(10): 3454-3469. |
[9] | 朱佳洁, 万义, 袁启洋, 魏金莲, 张永强. 可见光/路易斯碱协同催化的三氟甲基取代烯烃脱氟硅化反应研究[J]. 有机化学, 2023, 43(10): 3623-3634. |
[10] | 潘振涛, 刘彤, 马永敏, 颜剑波, 王亚军. 布朗斯特酸/可见光氧化还原接力催化构建喹唑啉(硫)酮[J]. 有机化学, 2022, 42(9): 2823-2831. |
[11] | 李亚东, 吴鹏举, 杨志勇. 可见光催化苯并噁唑与α-酮酸合成芳基苯并噁唑[J]. 有机化学, 2022, 42(6): 1770-1777. |
[12] | 孙天义, 张依凡, 孟远倢, 王怡, 朱琦峰, 姜玉新, 刘石惠. 可见光-铜共催化的糖类区域选择性氧烷基化反应[J]. 有机化学, 2022, 42(5): 1414-1422. |
[13] | 李猛, 赵冬阳, 孙凯. 可见光驱动基团迁移引发的烯烃双官能团化反应[J]. 有机化学, 2022, 42(12): 4152-4168. |
[14] | 何燕, 黄天姿, 史小琴, 陈艳, 吴琼. 异腈参与的光催化反应研究进展[J]. 有机化学, 2022, 42(12): 4220-4246. |
[15] | 杨惜晖, 高皓炜, 闫甲乐, 史雷. 自由基介导的硅烷Si—H键官能团化研究进展: 一种合成含C—Si键有机硅化合物的有效策略[J]. 有机化学, 2022, 42(12): 4122-4151. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||