Visible Light Photoredox Catalysis Mediated Elementary Steps in Organometallic Reactions

doi:10.6023/cjoc201704030

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2203-2210.DOI: 10.6023/cjoc201704030 Previous Articles Next Articles

REVIEW

可见光催化促进的金属有机基元反应

吴江^b, 李嘉雯^a, 李昊^a, 朱纯银^a

a 江苏大学化学化工学院镇江 212013;
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2017-04-18 修回日期:2017-05-22 发布日期:2017-06-07
通讯作者: 朱纯银 E-mail:zhucycn@gmail.com
基金资助:
江苏省"青蓝工程"中青年学术带头人培养对象资助项目.

Visible Light Photoredox Catalysis Mediated Elementary Steps in Organometallic Reactions

Wu Jiang^b, Li Jiawen^a, Li Hao^a, Zhu Chunyin^a

a School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013;
b State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2017-04-18 Revised:2017-05-22 Published:2017-06-07
Contact: 10.6023/cjoc201704030 E-mail:zhucycn@gmail.com
Supported by:
Project supported by the Qing Lan Project of Jiangsu Province.

Many organometallic reactions involve three elementary steps including oxidative addition, transamination, and reductive elimination. But sometimes very high barrier exists for this approach, leading to the failure of the reactions. The key development in recent reports is the implementation of visible-light photocatalysts as a means to induce the desired redox processes in a mild and selective manner. In this context, organometallic reactions mediated by photoredox catalysts could give rise to novel reactivity, thus this area has drawn much attention in organic chemistry community. In this review, prominent examples from the recent literatures are organized on the basis of the elementary transformation enabled by photoredox catalysis.

Key words: organometallic reactions, elementary steps, visible light photoredox

Cite this article

Wu Jiang, Li Jiawen, Li Hao, Zhu Chunyin. Visible Light Photoredox Catalysis Mediated Elementary Steps in Organometallic Reactions[J]. Chin. J. Org. Chem., 2017, 37(9): 2203-2210.

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[1] (a) Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
(b) Hartwig, J. F. Organotransition Metal Chemistry:From Bonding to Catalysis, University Science Books, Herndon, VA, 2010.
[2] For selected reviews on photoredox catalysis:
(a) Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828.
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322.
(c) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176.
(d) Angnes, R. A.; Li, Z.; Correia, C. R. D.; Hammond, G. B. Org. Biomol. Chem. 2015, 13, 9152.
(e) Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632.
(f) Luo, J.; Zhang, J. ACS Catal. 2016, 6, 873.
(g) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044.
(h) Lang, X.; Zhao, J.; Chen X., Chem. Soc. Rev. 2016, 45, 3026.
(i) Levin, M. D.; Kim, S.; Toste, F. D. ACS Cent. Sci. 2016, 2, 293.
(j) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
(d) Hopkinson, M. N.; Tlahuext-Aca, A.; Glorius, F. Acc. Chem. Res. 2016, 49, 2261.
(k) Tellis, J. C.; Kelly, C. B.; Primer, D. N.; Jouffroy, M.; Patel, N. R.; Molander, G. A. Acc. Chem. Res. 2016, 49, 1429.
(l) Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522.
(m) Fabry, D.-C.; Rueping, M. Acc. Chem. Res. 2016, 49, 1969.
(n) Zhang, M.; Zhu, C.; Ye, L.-W. Synthesis 2017, 1150.
(o) Zuo, X.; Wu, W.-L.; Su, W.-P. Acta Chim. Sinica 2015, 73, 1298(in Chinese). (左璇, 吴文亮, 苏伟平, 化学学报, 2015, 73, 1298.)
(p) Guan, B.-C.; Xu, X.-L.; Wang, H.; Li, X.-N. Chin. J. Org. Chem. 2016, 36, 1564(in Chinese). (关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
(q) Tan, F.; Xiao, W.-J. Acta Chim. Sinica 2015, 73, 85(in Chinese). (谭芬, 肖文精, 化学学报, 2015, 73, 85.)
(r) Roh, G.-B.; Iqbal N.; Cho. E. J. Chin. J. Chem. 2016, 34, 459.
[3] Halpern, J. Acc. Chem. Res. 1970, 3, 386.
[4] Hill, R. H.; Puddephatt, R. J. J. Am. Chem. Soc. 1985, 107, 1218.
[5] (a) Johnson, A.; Puddephatt, R. J. J. Chem. Soc., Dalton Trans. 1976, 1360.
(b) Winston, M. S.; Wolf, W. J.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 7777.
[6] (a) Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566.
(b) Neufeldt, S. R.; Sanford, M. S. Adv. Synth. Catal. 2012, 354, 3517.
[7] Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505.
[8] Hopkinson, M. N.; Sahoo, B.; Glorius, F. Adv. Synth. Catal. 2014, 356, 2794.
[9] Xia, Z.; Khaled, O.; Mouriès-Mansuy, V.; Ollivier, C.; Fensterbank, L. J. Org. Chem. 2016, 81, 7182.
[10] Shu, X.-Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844.
[11] Um, J.; Yun, H.; Shin, S. Org. Lett. 2016, 18, 484.
[12] Tlahuext-Aca, A.; Hopkinson, M. N.; Garza-Sanchez, R. A.; Glorius, F. Chem.-Eur. J. 2016, 22, 5909.
[13] Alcaide, B.; Almendros, P.; Busto, E.; Luna, A. Adv. Synth. Catal. 2016, 358, 1526.
[14] He, Y.; Wu, H.; Toste, F. D. Chem. Sci. 2015, 6, 1194.
[15] Tlahuext-Aca, A.; Hopkinson, M. N.; Sahoo, B.; Glorius, F. Chem. Sci. 2016, 7, 89.
[16] Kim, S.; Rojas-Martin, J.; Toste, F. D. Chem. Sci. 2016, 7, 85.
[17] Cornilleau, T.; Hermange, P.; Fouquet, E. Chem. Commun. 2016, 52, 10040.
[18] Gauchot, V.; Lee, A.-L. Chem. Commun. 2016, 52, 10163.
[19] (a) Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
(b) Le, C. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11938.
(c) Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 624.
[20] (a) Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330.
(b) Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929.
[21] Xuan, J.; Zeng, T.; Chen, J.; Lu, L.; Xiao, W. Chem.-Eur. J. 2015, 21, 4962.
[22] (a) Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
(b) El Khatib, M.; Serafim, R. A. M.; Molander, G. A. Angew. Chem., Int. Ed. 2016, 55, 254.
(c) Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2015, 137, 2195.

可见光催化促进的金属有机基元反应

Visible Light Photoredox Catalysis Mediated Elementary Steps in Organometallic Reactions

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