Photo-induced Catalytic Asymmetric Free Radical Reactions

doi:10.6023/A16080418

Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (1): 22-33.DOI: 10.6023/A16080418 Previous Articles Next Articles

Special Issue: 有机光化学

Perspective

催化不对称光诱导自由基反应

王德红^a,b, 张龙^a,b, 罗三中^a,b

a 中国科学院化学研究所分子识别与功能院重点实验室北京 100190;
b 中国科学院大学北京 100049

投稿日期:2016-08-16 修回日期:2016-09-13 发布日期:2016-09-18
通讯作者: 罗三中,E-mail:luosz@iccas.ac.cn;Tel.:0086-010-62554446 E-mail:luosz@iccas.ac.cn
作者简介:王德红:中国科学院化学研究所2013级在读硕博生,本科就读于东北师范大学.现在主要研究光催化和伯胺催化的不对称转化反应;张龙:中国科学院化学研究所分子识别与功能重点实验室副研究员.主要从事不对称光催化、仿生伯胺催化及其理论计算研究;罗三中:中国科学院化学研究所研究员、博士生导师,分子识别与功能重点实验室副主任.主要从事仿生小分子催化合成和物理有机研究.
基金资助:
项目受国家自然科学基金（Nos.21572232，21390400）资助.

Photo-induced Catalytic Asymmetric Free Radical Reactions

Wang Dehong^a,b, Zhang Long^a,b, Luo Sanzhong^a,b

a Key Laboratory of Molecular Recognition and Functions, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2016-08-16 Revised:2016-09-13 Published:2016-09-18
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572232, 21390400).

Enantioselective control of free radical reactions has eluded organic chemists for decades. Echoed with the renaissance of photo-induced processes, or so called photocatalysis or photoredox catalysis in organic synthesis, photo-induced organic radical chemistry has regained its prominence in developing catalytic asymmetric radical reaction. The generally mild conditions inherited with photochemistry, particularly visible light photo-processes, have allowed for controllable generation of free radicals as well as the subsequent bond formations. The past five years have witnessed dramatic advances in exploring photo-induced catalytic asymmetric free radical reactions, and enormous potentials along this line are envisaged. This perspective gives a brief summary on the important advances in this field. Accordingly, the major advances are classified based on different radical species including α-amino/oxyl radicals, radicals generated from enones and its analogues, benzyl radicals, α-carbonyl radicals, polyhalogenated alkyl radicals and nitrogen radicals. Brief discussion of mechanism is presented whenever relevant.

Key words: photoredox catalysis, free radical reaction, asymmetric catalysis, synergistic catalysis

Cite this article

Wang Dehong, Zhang Long, Luo Sanzhong. Photo-induced Catalytic Asymmetric Free Radical Reactions[J]. Acta Chim. Sinica, 2017, 75(1): 22-33.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Parsons, A. F. An Introduction to Free Radical Chemistry, Wiley-Blackwell, Hoboken, New Jersey, 2000.
(b) Renaud, P.; Sibi, M. P. Radicals in Organic Synthesis, Wiley-VCH, Weinheim, 2001.
(c) Shang, X.; Liu, Z. Acta Chim. Sinica 2015, 73, 1275. (尚筱洁, 柳忠全, 化学学报, 2015, 73, 1275.)
[2] (a) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
(b) Zimmerman, J.; Sibi, M. P. Enantioselective Radical Reactions. In Radicals in Synthesis I, Springer, Berlin, Heidelberg, 2006, pp. 107~162.
[3] (a) Beeson, T. D.; Mastracchio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. Science 2007, 316, 582.
(b) Comito, R. J.; Finelli, F. G.; MacMillan, D. W. J. Am. Chem. Soc. 2013, 135, 9358.
(c) Jui, N. T.; Garber, J. A.; Finelli, F. G.; MacMillan, D. W. J. Am. Chem. Soc. 2012, 134, 11400.
(d) Pham, P. V.; Ashton, K.; MacMillan, D. W. Chem. Sci. 2011, 2, 1470.
(e) Mastracchio, A.; Warkentin, A. A.; Walji, A. M.; MacMillan, D. W. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20648.
(f) Devery, J. J.; Conrad, J. C.; MacMillan, D. W.; Flowers, R. A. Angew. Chem. Int. Ed. 2010, 49, 6106.
(g) Jui, N. T.; Lee, E. C.; MacMillan, D. W. J. Am. Chem. Soc. 2010, 132, 10015.
(h) Van Humbeck, J. F.; Simonovich, S. P.; Knowles, R. R.; MacMillan, D. W. J. Am. Chem. Soc. 2010, 132, 10012.
(i) Devery, J. J.; Conrad, J. C.; MacMillan, D. W.; Flowers, R. A. J. Am. Chem. Soc. 2010, 132, 6106.
(j) Rendler, S.; MacMillan, D. W. J. Am. Chem. Soc. 2010, 132, 5027.
(k) Wilson, J. E.; Casarez, A. D.; MacMillan, D. W. J. Am. Chem. Soc. 2009, 131, 11332.
(l) Conrad, J. C.; Kong, J.; Laforteza, B. N.; MacMillan, D. W. J. Am. Chem. Soc. 2009, 131, 11640.
(m) Amatore, M.; Beeson, T. D.; Brown, S. P.; MacMillan, D. W. Angew. Chem. Int. Ed. 2009, 48, 5121.
(n) Graham, T. H.; Jones, C. M.; Jui, N. T.; MacMillan, D. W. J. Am. Chem. Soc. 2008, 130, 16494.
(o) Kim, H.; MacMillan, D. W. J. Am. Chem. Soc. 2008, 130, 398.
(p) Jang, H. Y.; Hong, J. B.; MacMillan, D. W. J. Am. Chem. Soc. 2007, 129, 7004.
[4] For selected reviews, see:(a) Peñ-López, M.; Rosas-Hernández, A.; Beller, M. Angew. Chem. Int. Ed. 2015, 54, 5006.
(b) Hopkinson, M. N.; Sahoo, B.; Li, J. L.; Glorius, F. Chem. Eur. J. 2014, 20, 3874.
(c) Hari, D. P.; König, B. Angew. Chem. Int. Ed. 2013, 52, 4734.
(d) Xuan, J.; Lu, L. Q.; Chen, J. R.; Xiao, W. J. Eur. J. Org. Chem. 2013, 6755.
(e) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387.
(f) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322.
(g) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687.
(h) Xuan, J.; Xiao, W. J. Angew. Chem. Int. Ed. 2012, 51, 6828.
(i) Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102.
(j) Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859.
(k) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
(l) Acta Chim. Sinica 2015, 73, 85. (谭芬, 肖文精, 化学学报, 2015, 73, 85.)
[5] Ruiz Espelt, L.; McPherson, I. S.; Wiensch, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2015, 137, 2452.
[6] Lenhart, D.; Bauer, A.; Pöthig, A.; Bach, T. Chem. Eur. J. 2016, 22, 6519.
[7] Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139.
[8] Murphy, J. J.; Bastida, D.; Paria, S.; Fagnoni, M.; Melchiorre, P. Nature 2016, 532, 218.
[9] Uraguchi, D.; Kinoshita, N.; Kizu, T.; Ooi, T. J. Am. Chem. Soc. 2015, 137, 13768.
[10] (a) Wang, C.; Qin, J.; Shen, X.; Riedel, R.; Harms, K.; Meggers, E. Angew. Chem. Int. Ed. 2016, 55, 685.
(b) Ma, J.; Harms, K.; Meggers, E. Chem. Commun. 2016, 52, 10183.
[11] Zuo, Z.; Cong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. J. Am. Chem. Soc. 2016, 138, 1832.
[12] Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735.
[13] (a) Du, J.; Skubi, K. L.; Schultz, D. M.; Yoon, T. P. Science 2014, 344, 392.
(b) Amador, A. G.; Sherbrook, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2016, 138, 4722.
[14] Shih, H. W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. J. Am. Chem. Soc. 2010, 132, 13600.
[15] Huo, H.; Shen, X.; Wang, C.; Zhang, L.; Röse, P.; Chen, L. A.; Meggers, E. Nature 2014, 515, 100.
[16] (a) Arceo, E.; Jurberg, I. D.; Álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750.
(b) Arceo, E.; Bahamonde, A.; Bergonzini, G.; Melchiorre, P. Chem. Sci. 2014, 5, 2438.
[17] Huo, H.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2016, 138, 6936.
[18] (a) Nicewicz, D. A.; MacMillan, D. W. Science, 2008, 322, 77.
(b) Zhu, Y.; Zhang, L.; Luo, S. J. Am. Chem. Soc. 2014, 136, 14642.
[19] Silvi, M.; Arceo, E.; Jurberg, I. D.; Cassani, C.; Melchiorre, P. J. Am. Chem. Soc. 2015, 137, 6120.
[20] Kainz, Q. M.; Matier, C. D.; Bartoszewicz, A.; Zultanski, S. L.; Peters, J. C.; Fu, G. C. Science 2016, 351, 681.
[21] Nagib, D. A.; Scott, M. E.; MacMillan, D. W. J. Am. Chem. Soc. 2009, 131, 10875.
[22] Huo, H.; Wang, C.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2015, 137, 9551.
[23] Wo?niak, ?.; Murphy, J. J.; Melchiorre, P. J. Am. Chem. Soc. 2015, 137, 5678.
[24] (a) Cecere, G.; König, C. M.; Alleva, J. L.; MacMillan, D. W. J. Am. Chem. Soc. 2013, 135, 11521.
(b) Shen, X.; Harms, K.; Marsch, M.; Meggers, E. Chem. Eur. J. 2016, 22, 9102.

催化不对称光诱导自由基反应

Photo-induced Catalytic Asymmetric Free Radical Reactions

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Zhanglong Yu, Zhongliang Li, Changjiang Yang, Qiangshuai Gu, Xinyuan Liu. Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★ [J]. Acta Chimica Sinica, 2023, 81(8): 955-966.
[2]	Shuang Yang, Ningyi Wang, Qingqing Hang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★ [J]. Acta Chimica Sinica, 2023, 81(7): 793-808.
[3]	Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li. Gold/Iridium Catalyzed Alkynylamide Cyclization/Asymmetric Allylic Benzylation Cascade Reaction^★ [J]. Acta Chimica Sinica, 2023, 81(5): 431-434.
[4]	Qingduan Meng, Jiahong Han, Yixiao Pan, Wei Hao, Qing-Hua Fan. Asymmetric Synthesis of C₁-Symmetric Chiral N-Heterocyclic Carbene (NHC) Ligands and Their Applications in Asymmetric Catalysis^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1271-1279.
[5]	Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes [J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164.
[6]	Jinyue Ma, Lufei Huang, Baowen Zhou, Lin Yao. Construction and Catalysis Advances of Inorganic Chiral Nanostructures [J]. Acta Chimica Sinica, 2022, 80(11): 1507-1523.
[7]	Qing-Ru Zhao, Ru Jiang, Shu-Li You. Ir-catalyzed Sequential Asymmetric Allylic Substitution/Olefin Isomerization for the Synthesis of Axially Chiral Compounds [J]. Acta Chimica Sinica, 2021, 79(9): 1107-1112.
[8]	Caixia Guo, Xiaojie Ma, Bo Wang. Metal-organic Frameworks-based Composites and Their Photothermal Applications [J]. Acta Chimica Sinica, 2021, 79(8): 967-985.
[9]	Bo-Shuai Mu, Zhi-Hao Zhang, Wen-Biao Wu, Jin-Sheng Yu, Jian Zhou. Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines [J]. Acta Chimica Sinica, 2021, 79(6): 685-693.
[10]	Hongshao Jia, Baokun Qiao, Zhiyong Jiang. Photoredox Catalytic Radical Coupling to Access β-Fluoro α-Amino Acid Derivatives [J]. Acta Chimica Sinica, 2021, 79(12): 1477-1480.
[11]	Yi Li, Ming-Hua Xu. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines [J]. Acta Chimica Sinica, 2021, 79(11): 1345-1359.
[12]	Zhao, Yong, Li, Shihong, Zhang, Miaomiao, Liu, Feng. Synthesis of β,γ-Unsaturated Esters and γ-Ketone Esters with Amino Acid Ester-Derived Katritzky Salts [J]. Acta Chimica Sinica, 2019, 77(9): 916-921.
[13]	Liu, Yu-Cheng, Zheng, Xiao, Huang, Pei-Qiang. Photoredox Catalysis for the Coupling Reaction of Nitrones with Aromatic Tertiary Amines [J]. Acta Chimica Sinica, 2019, 77(9): 850-855.
[14]	Zhang, Zhen, Gong, Li, Zhou, Xiao-Yu, Yan, Si-Shun, Li, Jing, Yu, Da-Gang. Radical-Type Difunctionalization of Alkenes with CO₂ [J]. Acta Chimica Sinica, 2019, 77(9): 783-793.
[15]	Zhang, Hong-Hao, Yu, Shouyun. Advances on Transition Metals and Photoredox Cooperatively Catalyzed Allylic Substitutions [J]. Acta Chimica Sinica, 2019, 77(9): 832-840.