可见光催化炔烃串联氰基烷基磺酰化/环化

doi:10.6023/cjoc202102051

有机化学 ›› 2021, Vol. 41 ›› Issue (6): 2290-2301.DOI: 10.6023/cjoc202102051 上一篇下一篇

所属专题：有机光催化虚拟合辑；热点论文虚拟合集

研究论文

可见光催化炔烃串联氰基烷基磺酰化/环化

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

a 湖南理工学院化学化工学院湖南岳阳 414006
b 湖南师范大学湖南省有机功能分子组装与应用重点实验室长沙 410081

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:
国家自然科学基金(22078084); 国家自然科学基金(51874132); 湖南省教育厅科学研究基金(20A224); 湖南省教育厅科学研究基金(20A213); 湖南省教育厅科学研究基金(18B355); 湖南省科技计划项目(2020RC3056); 湖南省科技计划项目(2018TP1017); 湖南省自然科学基金(2020JJ5221); 湖南省自然科学基金(2020JJ5212)

Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes

Yu Liu^a^,^b, Zan Chen^a, Pu Chen^a, Biquan Xiong^a, Jun Xie^a(), An Liu^a(), Yun Liang^b, Kewen Tang^a

a Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006
b Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081

Received:2021-02-27 Revised:2021-03-18 Published:2021-03-25
Contact: Jun Xie, An Liu
Supported by:
National Natural Science Foundation of China(22078084); National Natural Science Foundation of China(51874132); Scientific Research Fund of Hunan Provincial Education Department(20A224); Scientific Research Fund of Hunan Provincial Education Department(20A213); Scientific Research Fund of Hunan Provincial Education Department(18B355); Science and Technology Planning Project of Hunan Province(2020RC3056); Science and Technology Planning Project of Hunan Province(2018TP1017); Natural Science Foundation of Hunan Province(2020JJ5221); Natural Science Foundation of Hunan Province(2020JJ5212)

文章分享

1. 212290S.pdf(13221KB)

摘要/Abstract

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.

关键词: 可见光催化, SO₂插入, 环酮肟酯, N-炔丙基吲哚

A transition-metal-free visible-light-mediated tandem cyanoalkylsulfonylation/cyclization of alkynes with cycloketone oxime derivatives for the construction of 2-cyanoalkylsulfonyl-9H-pyrrolo[1,2-a]indoles through the insertion of SO₂ is reported. The difunctionalization of carbon-carbon triple bonds includes a radical mechanism and undergoes the formation of iminyl radical, ring-opening of cycloketone, insertion of SO₂, addition of sulfonyl radical to carbon-carbon triple bonds, intramolecular cyclization and isomerization.

Key words: visible-light-catalysis, the insertion of SO₂, cycloketone oxime esters, N-propargylindoles

引用此文

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 6

参考文献 21

[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.

可见光催化炔烃串联氰基烷基磺酰化/环化

Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 6

参考文献 21

相关文章 15

编辑推荐

相关统计

本文评价

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
10^c	Na₂S₂O₅ instead of K₂S₂O₅	73
11^c	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
19^c	DMF instead of CH₃CN	27
20^c	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
28^d	None	52

[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.