Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor

doi:10.1007/s40242-021-1413-y

Chemical Research in Chinese Universities ›› 2022, Vol. 38 ›› Issue (2): 505-509.doi: 10.1007/s40242-021-1413-y

• Letters • Previous Articles Next Articles

Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor

ZHANG Tingting^1,2, LUO Pan^1,2, LAI Can^1,2, LIU Zheyi¹, JIN Yan¹, WANG Fangjun^1,2

1. CAS Key Laboratory of Separation Sciences for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received:2021-10-11 Revised:2021-11-22 Online:2022-04-01 Published:2021-11-24
Contact: WANG Fangjun E-mail:wangfj@dicp.ac.cn
Supported by:
This work was supported by the National Key R&D Program of China(No. 2019YFE0119300), the National Natural Science Foundation of China(Nos. 32088101, 91853101), the Grant from Chinese Academy of Sciences(No.ZDBSLY-SLH032), the Natural Science Foundation of Liaoning Province, China(No. 2019-YQ-07), the Dalian Science and Technology Innovation Foundation, China (No.2019J11CY019), and the Grant from Dalian Institute of Chemical Physics, CAS(No.DICP I202007).

Abstract

ZHANG Tingting, LUO Pan, LAI Can, LIU Zheyi, JIN Yan, WANG Fangjun. Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor[J]. Chemical Research in Chinese Universities, 2022, 38(2): 505-509.

References

[1] Gosmini C., Moncomble A., Isr. J. Chem., 2010, 50(5/6), 568.
[2] Liegault B., Lapointe D., Caron L., Vlassova A., Fagnou K., J. Org. Chem., 2009, 74(5), 1826.
[3] Lorpaiboon W., Bovonsombat P., Org. Biomol. Chem., 2021, 19(35), 7518.
[4] Satpute D. P., Vaidya G. N., Lokhande S. K., Shinde S. D., Bhujbal S. M., Chatterjee D. R., Rana P., Venkatesh A., Nagpure M., Kumar D., Green Chem., 2021, 23(17), 6273.
[5] Li L., Liu W., Mu X., Mi Z., Li C. J., Nat. Protoc., 2016, 11(10), 1948.
[6] Prier C. K., Rankic D. A., MacMillan D. W., Chem. Rev., 2013, 113(7), 5322.
[7] Saikia I., Borah A. J., Phukan P., Chem. Rev., 2016, 116(12), 6837.
[8] Ma D. W., Xia C. F., Jiang J. Q., Zhang J. H., Org. Lett., 2001, 3(14), 2189.
[9] Ghosh S., Shashidhar J., Tetrahedron Lett., 2009, 50(11), 1177.
[10] Varenikov A., Shapiro E., Gandelman M., Chem. Rev., 2021, 121(1), 412.
[11] Cresswell A. J., Eey S. T., Denmark S. E., Angew. Chem. Int. Ed., 2015, 54(52), 15642.
[12] Song S., Sun X., Li X., Yuan Y., Jiao N., Org. Lett., 2015, 17(12), 2886.
[13] Rogers D. A., Brown R. G., Brandeburg Z. C., Ko E. Y., Hopkins M. D., LeBlanc G., Lamar A. A., ACS Omega, 2018, 3(10), 12868.
[14] Kathiravan S., Nicholls I. A., Chem. Eur. J., 2017, 23(29), 7031.
[15] Romero N. A., Nicewicz D. A., Chem. Rev., 2016, 116(17), 10075.
[16] Fan J., Wei Q., Zhu E., Gao J., Cheng X., Lu Y., Loh T. P., Chem. Commun., 2021, 57(48), 5977.
[17] Ohkubo K., Mizushima K., Iwata R., Fukuzumi S., Chem. Sci., 2011, 2(4), 715.
[18] Petzold D., König B., Adv. Synth. Catal., 2018, 360(4), 626.
[19] Ramachandran M. S., Easwaramoorthy D., Vasanthkumar S., J. Org. Chem., 1996, 61(13), 4336.
[20] Ramachandran M. S., Easwaramoorthy D., Rajasingh V., Vivekanandam T. S., Bull. Chem. Soc. Jpn., 1990, 63(8), 2397.
[21] Gopalakrishnan G., Hogg J. L., J. Org. Chem., 1985, 50(8), 1206.
[22] Yokoyama Y., Yamaguchi T., Sato M., Kobayashi E., Murakami Y., Okuno H., Chem. Pharm. Bull.(Tokyo), 2006, 54(12), 1715.
[23] Li L., Liu W., Zeng H., Mu X., Cosa G., Mi Z., Li C. J., J. Am. Chem. Soc., 2015, 137(26), 8328.
[24] Yuan Y., Yao A., Zheng Y., Gao M., Zhou Z., Qiao J., Hu J., Ye B., Zhao J., Wen H., Lei A., iScience, 2019, 12, 293.
[25] Song S., Li X., Wei J., Wang W., Zhang Y., Ai L., Zhu Y., Shi X., Zhang X., Jiao N., Nat. Catal., 2019, 3(2), 107.
[26] Obst M., Shaikh R. S., König B., Reaction Chemistry& Engineering, 2017, 2(4), 472.
[27] Houghton J. A., Lee G., Am. Ind. Hyg. Assoc. J., 1961, 22, 296.
[28] Spiesecke H., Schneider W. G., J. Chem. Phys., 1961, 35(2), 731.
[29] Hansch C., Leo A., Taft R. W., Chem. Rev., 2002, 91(2), 165.
[30] Sato S., Nakamura H., Angew. Chem. Int. Ed. Engl., 2013, 52(33), 8681.
[31] Alvarez Dorta D., Deniaud D., Mevel M., Gouin S. G., Chem. Eur. J., 2020, 26(63), 14257.
[32] Krygowski T. M., Dobrowolski M. A., Zborowski K., Cyrański M. K., J. Phys. Org. Chem., 2006, 19(12), 889.
[33] Li L., Mu X., Liu W., Wang Y., Mi Z., Li C. J., J. Am. Chem. Soc., 2016, 138(18), 5809.
[34] Basle E., Joubert N., Pucheault M., Chem. Biol., 2010, 17(3), 213.
[35] Sakamoto S., Hamachi I., Anal. Sci., 2019, 35(1), 5.
[36] Kee C. W., Tack O., Guibbal F., Wilson T. C., Isenegger P. G., Imiolek M., Verhoog S., Tilby M., Boscutti G., Ashworth S., Chupin J., Kashani R., Poh A. W. J., Sosabowski J. K., Macholl S., Plisson C., Cornelissen B., Willis M. C., Passchier J., Davis B. G., Gouverneur V., J. Am. Chem. Soc., 2020, 142(3), 1180.
[37] Cardinal P., Greer B., Luong H., Tyagunova Y., J. Chem. Educ., 2012, 89(8), 1061.
[38] Lu L., Li Y., Jiang X., Green Chem., 2020, 22(18), 5989.
[39] Cernak T., Dykstra K. D., Tyagarajan S., Vachal P., Krska S. W., Chem. Soc. Rev., 2016, 45(3), 546.

Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 8

Recommended Articles

Metrics

Comments

[1]	CHU Ning, XU Shuping, XU Weiqing. Catalyst-free 2+2 Photodimerization of 1,4-Bis[2-(4-pyridyl)ethenyl]-benzene in Solution Under Low Power UV Irradiation [J]. Chemical Research in Chinese Universities, 2020, 36(5): 816-820.
[2]	ZENG Ruijie, SHENG Hongting, RAO Bo, FENG Yan, WANG Hao, SUN Yehua, CHEN Man, ZHU Manzhou. An Efficient and Green Approach to Synthesizing Enamines by Intermolecular Hydroamination of Activated Alkynes [J]. Chemical Research in Chinese Universities, 2015, 31(2): 212-217.
[3]	CHEN Zhanguo, LIU Yali, HU Junli, LIU De'e. Aminobromination of Ethyl α-Cyanocinnamate Derivatives with 1,3-Dibromo-5,5-dimethylhydantoin(DBDMH) as Nitrogen and Halogen Sources [J]. Chemical Research in Chinese Universities, 2015, 31(1): 65-70.
[4]	REN Dong-xue, CAO Yun-zhu, CHEN Chen, XING Yong-heng. Vanadium Haloperoxidases Model Compounds: Synthesis, Structural Characterization and Mimic Catalytic Bromination Activity of [VO(C₂O₄)(2,2′-bipy)(H₂O)]·C₂H₅OH and VO(C₂O₄)(phen)(H₂O) [J]. Chemical Research in Chinese Universities, 2012, 28(5): 768-774 .
[5]	PENG Fei, XUE Hong-hai, TANG Xiao-jian, KANG Chun-li, LI Lin-lin, LI Zhe. Comparison of Photochemical Reactions of m-Cresol in Aqueous Solution and in Ice [J]. Chemical Research in Chinese Universities, 2012, 28(1): 47-52.
[6]	MAJID Kowsar , AHMAD Siraj , MALIK Mukhtar Ahmad. Novel Photoinitiated Synthesis, Characterization, Thermal Kinetics, and Mechanism of Complex of Potassium Hexacyanoferrate with Imidazole [J]. Chemical Research in Chinese Universities, 2009, 25(2): 138-142.
[7]	LI Pin-hua, RAO Wan-ping, WANG Min, WANG Lei. Ultrasonic-enhanced Stereoselective Debromination of vic-Dibromides to Alkenes with Metallic Zinc Powder in Aqueous Media [J]. Chemical Research in Chinese Universities, 2004, 20(5): 598-601.
[8]	Yu Hengtai, Shen Erzhong, Ye Yuanjie, Zhang Gang. A Theoretical Study of Photochemical Reaction for Synthesis of Thiirane [J]. Chemical Research in Chinese Universities, 1988, 4(3): 40-45.