化学反应溶剂的绿色化是绿色化学发展的必然趋势,利用储量丰富、廉价易得、无毒性、无污染的水替代传统有机溶剂作为反应介质是化学家们追求的目标。自由基反应由于反应活性高、反应条件温和,逐渐成为有机合成的一种重要策略。本文依据所构建化学键类型的不同,对近5年来水介质中的有机自由基反应研究进展进行了综述。
The greenization of chemical reaction solvent is an inevitable trend of green chemistry in the future. And it is the goal of chemists to replace the traditional organic solvents with water which is abundant, cheap, non-toxic and pollution-free. Radical reaction has gradually become an important strategy for organic synthesis due to its high activity and mild reaction conditions. This review summarizes the advancements of organic radical reaction in water medium in recent five years on the basis of different chemical bonds.
Contents
1 Introduction
2 The construction of C-C bonds
3 The construction of C-N bonds
4 The construction of C-O bonds
5 The construction of C-S bonds
6 Conclusion
[1] Andrade C K Z, Alves L M. Curr. Org. Chem., 2005, 9:195.
[2] Simon M O, Li C J. Chem. Soc. Rev., 2012, 41:1415.
[3] Sheldon R A. Green Chem., 2005, 7:267.
[4] 李正凯(Li Z K), 吴之清(Wu Z Q), 邓杭(Deng H), 周向葛(Zhou X G). 有机化学(Chinese Journal of Organic Chemistry), 2013, 33:760.
[5] Lipshutz B H, Gallou F, Handa S. ACS Sustain. Chem. Eng., 2016, 4:5838.
[6] Li Z, Ke F, Deng H, Xu H, Xiang H, Zhou X. Org. Biomol. Chem., 2013, 11:2943.
[7] 宋河远(Song H Y), 康美荣(Kang M R), 靳荣华(Jin R H), 金福祥(Jin F X), 陈静(Chen J). 化学进展(Progress in Chemistry), 2016, 28(9):1313.
[8] Wang X S, Sheng J, Lu L, Yang K, Li Y L. ACS Comb. Sci., 2011, 13:196.
[9] Leitner W. Acc. Chem. Res., 2002, 35:746.
[10] Feng X J, Yan M, Zhang T, Liu Y, Bao M. Green Chem., 2010, 12:1758.
[11] Du Z, Zhou W, Bai L, Wang F, Wang J X. Synlett, 2011, 369.
[12] Chen J, Spear S K, Huddleston J G. Green Chem., 2005, 7:64.
[13] Wang F, Chen C, Deng G, Xi C J. J. Org. Chem., 2012, 77:4148.
[14] Zard S Z. Chem. Soc. Rev., 2008, 37:1603.
[15] Staveness D, Bosque I, Stephenson C R J. Acc. Chem. Res., 2016, 49:2295.
[16] Deng G B, Zhang J L, Liu Y Y, Liu B, Yang X H, Li J H. Chem. Commun., 2015, 51:1886.
[17] Kilpatrick B, Heller M, Arns S. Chem. Commun., 2013, 49:514.
[18] Mao S, Gao Y R, Zhu X Q, Guo D D, Wang Y Q. Org. Lett., 2015, 17:1692.
[19] Zhao Y T, Huang B B, Yang C, Xia W J. Org. Lett., 2016, 18:3326.
[20] Postigo A. Curr. Org. Chem., 2009, 13:1683.
[21] Perchyonoka V T, Lykakisb I N. Curr. Org. Chem., 2009, 13:573.
[22] Wei W T, Zhu W M, Ying W W, Wang Y N, Bao W H, Gao L H, Luo Y J, Liang H Z. Adv. Synth. Catal., 2017, 359:3551.
[23] Ying W W, Zhu W M, Liang H Z, Wei W T. Synlett, 2018, 29:215.
[24] Zhu W M, Bao W H, Ying W W, Chen W T, Huang Y L, Ge G P, Chen G P, Wei W T. Asian J. Org. Chem., 2018, 7:337.
[25] Wei W T, Zhu W M, Liang W D, Wu Y, Huang H Y, Huang Y L, Luo J F, Liang H Z. Synlett, 2017, 28:2153.
[26] Wei W T, Ying W W, Zhu W M, Wu Y, Huang Y L, Cao Y Q, Wang Y N, Liang H Z. Synlett, 2017, 28:2307.
[27] Li D D, Li Z Y, Wang G W. J. Org. Chem., 2015, 80:190.
[28] Zhu C, Yang B, Bäckvall J E. J. Am. Chem. Soc., 2015, 137:11868.
[29] Augustine R L. Carbon-Carbon Bond Formation. Dekker:New York, 1979.
[30] Naresh G, Kant R, Narender T. Org. Lett., 2015, 17:3446.
[31] Wu C J, Zhong J J, Meng Q Y, Lei T, Gao X W, Tung C H, Wu L Z. Org. Lett., 2015, 17:884.
[32] Li H, Liu C J, Zhang Y H, Sun Y D, Wang B, Liu W B. Org. Lett., 2015, 17:932.
[33] Cui L, Chen H, Liu C, Li C Z. Org. Lett., 2016, 18:2188.
[34] Xu J, Qiao L, Shen J B, Chai K J, Shen C, Zhang P F. Org. Lett., 2017, 19:5661.
[35] Shen H G, Liu Z L, Zhang P, Tan X Q, Zhang Z Z, Li C Z. J. Am. Chem. Soc., 2017, 139:9843.
[36] Ruiz-Castillo P, Buchwald S L. Chem. Rev., 2016, 116:12564.
[37] Cho H S, Kim J Y, Kwak J, Chang S. Chem. Soc. Rev., 2011, 40:5068.
[38] Ramirez T A, Zhao B, Shi Y. Chem. Soc. Rev., 2012, 41:931.
[39] Huang H, Chen W H, Xu Y, Li J. Green Chem., 2015, 17:4715.
[40] Sharma A, Hartwig J F. Nature, 2015, 29:600.
[41] 窦言东(Dou Y D), 应莎莎(Ying S S), 张晨卿(Zhang C Q), 余黎阳(Yu L Y), 郑垦(Zheng K), 朱勍(Zhu Q). 化学进展(Progress in Chemistry), 2007, 29(02/3):293.
[42] Wang T, Yuan L, Zhao Z G, Shao A L, Gao M, Huang Y F, Xiong F, Zhang H L, Zhao J F. Green Chem., 2015, 17:2741.
[43] Liu C, Wang X Q, Li Z D, Cui L, Li C Z. J. Am. Chem. Soc., 2015, 137:9820.
[44] Natarajan P, Priya, Chuskit D. Green Chem., 2017, 19:5854.
[45] Deb M L, Pegu C D, Borpatra P J, Saikia P J, Baruah P K. Green Chem., 2017, 19:4036.
[46] Chylinska J B, Urbanski T, Mordarski M. J. Med. Chem., 1963, 6:484.
[47] Waisser K, Gregor K, Kubicova L, Klimesova V, Kunes J, Machacek M, Kaustova J. Eur.J. Med. Chem., 2000, 35:733.
[48] Petrlikova E, Waisser K, DiviSova H, Husakova P, Vrabcova P, Kunes J, Kolar K, Stolarikova J. Bioorg. Med. Chem., 2010, 18:8178.
[49] Wei W T, Zhu W M, Ying W W, Wu Y, Huang Y L, Liang H Z. Org. Biomol. Chem., 2017, 15:5254.
[50] Jiang Y Q, Li X F, Li X Y, Sun Y M, Zhao Y R, Jia S H, Guo N, Xu G Q, Zhang W W. Chin. J. Chem., 2017, 35:1239.
[51] Xu Z W, Yan P F, Jiang H, Liu K R, Zhang Z C. Chin. J. Chem., 2017, 35:581.
[52] Yu D G, Li B J, Shi Z J. Acc. Chem. Res., 2010, 43:1486.
[53] Hossain M M, Huang W K, Chen H J, Wang P H, Shyu S G. Green Chem., 2014, 16:3013.
[54] Ren L H, Wang L Y, Lv Y, Shang S S, Chen B, Gao S. Green Chem., 2015, 17:2369.
[55] Satheesh V, Sengoden M, Punniyamurthy T. J. Org. Chem., 2016, 81:9792.
[56] Dembitsky V M. Eur. J. Med. Chem. 2008, 43:223.
[57] Zmitek K, Zupan M, Iskra J. Org. Biomol. Chem., 2007, 5:3895.
[58] Kong D L, Cheng L, Yue T, Wu H R, Feng W C, Wang D, Liu L. J. Org. Chem., 2016, 81:5337.
[59] Xie H Y, Han L S, Huang S, Lei X T, Cheng Y, Zhao W F, Sun H B, Wen X A, Xu Q L. J. Org. Chem., 2017, 82:5236.
[60] Wu J L, Liu Y, Ma X W, Liu P, Gu C Z, Dai B. Chin. J. Chem., 2017, 35:1391.
[61] Wei W T, Zhu W M, Shao Q J, Bao W H, Chen W T, Chen G P, Luo J F, Liang H Z. ACS Sustainable Chem. Eng., 2018, 6:8029.
[62] Dondoni A. Angew. Chem. Int. Ed., 2010, 120:9133.
[63] Cole D C, Lennox W J, Lombardi S, Ellingboe J W, Bernotas R C, Tawa G J, Mazandarani H, Smith D L, Zhang G M, Coupet J, Schechter L E. J. Med. Chem., 2005, 48:353.
[64] Banerjee M, Poddar A, Mitra G, Surolia A, Owa T, Bhattacharyya B. J. Med. Chem., 2005, 48:547.
[65] 孙丰莉(Sun F L), 刘学民(Liu X M), 陈新志(Chen X Z), 钱超(Qiao C), 葛新(Ge X). 有机化学(Chinese Journal of Organic Chemistry), 2017, 37:2211.
[66] Zheng L, Zhou Z Z, He Y T, Li L H, Ma J W, Qiu Y F, Zhou P X, Liu X Y, Xu P F, Liang Y M. J. Org. Chem., 2016, 81:66.
[67] Yang Y, Bao Y J, Guan Q Q, Sun Q, Zha Z G, Wang Z Y. Green Chem., 2017, 19:112.
[68] Lai J Y, Yuan G Q. Tetrahedron Lett., 2017, 59:524.