Asymmetric Catalytic Carbon-Carbon Coupling Reactions via Cross-Dehydrogenative Coupling Reactions

doi:10.6023/cjoc201408030

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2406-2411.DOI: 10.6023/cjoc201408030 Previous Articles Next Articles

REVIEW

过渡金属催化的不对称交叉脱氢偶联反应研究进展

张艳, 冯柏年

江南大学药学院无锡 214122

收稿日期:2014-08-26 修回日期:2014-09-20 发布日期:2014-10-21
通讯作者: 冯柏年 E-mail:fengbainian@jiangnan.edu.cn
基金资助:
国家自然科学基金(No.21302067)和江苏省自然科学基金(No.BK20130120)资助项目.

Asymmetric Catalytic Carbon-Carbon Coupling Reactions via Cross-Dehydrogenative Coupling Reactions

Zhang Yan, Feng Bainian

School of Pharmaceutical Science, Jiangnan University, Wuxi 214122

Received:2014-08-26 Revised:2014-09-20 Published:2014-10-21
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21302067). and the Natural Science Foundation of Jiangsu Province (No. BK20130120).

Asymmetric catalytic C—C coupling reactions via cross-dehydrogenative coupling are currently among the most attractive and powerful tools in synthetic organic chemistry. In the past few decades, a variety of catalytic asymmetric C—C coupling reactions via cross-dehydrogenative coupling have been reported. Compared with traditional asymmetric C—C bond formation reactions, cross-dehydrogenative coupling strategies have more advantages in terms of power and cost-effectiveness. In this review, the recent studies on enantioselective cross dehydrogenative-coupling are reviewed.

Key words: asymmetric catalysis, cross-dehydrogenative coupling, C—H activation

Cite this article

Zhang Yan, Feng Bainian. Asymmetric Catalytic Carbon-Carbon Coupling Reactions via Cross-Dehydrogenative Coupling Reactions[J]. Chin. J. Org. Chem., 2014, 34(12): 2406-2411.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For selected reviews on metal-catalyzed cross-coupling reactions: (a) Diederich, F.; de Meijere, A. Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 2004. (b) Negishi, E. I.; de Meijere, A. Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley, New York, 2002. (c) Miyaura, N. A Practical Guide, Springer-Verlag, Berlin, 2002. (d) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions, Wiley, New York, 1998. (e) Beller, M.; Bolm, C. Bond Formation, Wiley-VCH, Wienheim, New York, 1997.
[2] Richard, F. Angew. Chem., Int. Ed. 2010, 49, 8300.
[3] For selected reviews on C—H bond functionalizations: (a) Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293. (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624. (c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. (d) Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Commun. 2010, 46, 677. (e) Thansandote, P.; Lautens, M. Chem. Eur. J. 2009, 15, 5874. (f) Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094. (g) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792. (h) Hartwig, J. F. Nature 2008, 455, 314. (i) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013. (j) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174. (k) Stuart, D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35. (l) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173. (m) Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036. (n) Bergman, R. G. Nature 2007, 446, 391. (o) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q. N.; Lazareva, A. Synlett 2006, 3382. (p) Godula, K.; Sames, D. Science 2006, 312, 67. (q) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077. (r) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731. (s) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (t) Jia, C. G.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (u) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698. (v) Yu, J. Q.; Shi, Z. Topics in Current Chemistry, Springer, Berlin, 2010, Vol. 292. (w) Dyker, G. Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2005. (x) Goldberg, K. I.; Goldman, A. S. Activation and Functionalization of C-H Bonds, American Chemical Society, Washington DC, 2004, Vol. 885.
[4] For related work on C-H activation/coupling reactions: (a) Qian, B.; Guo, S.; Shao, J.; Zhu, Q.; Yang, L.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2010, 132, 3650. (b) Qian, B.; Guo, S.; Xia, C.; Huang, H. Adv. Synth. Catal. 2010, 352, 3195. (c) Guo, S.; Qian, B.; Xie, Y.; Xia, C.; Huang, H. Org. Lett. 2011, 13, 522. (d) Qian, B.; Xie, P.; Xie, Y.; Huang, H. Org. Lett. 2011, 13, 2580. (e) Ynag, L.; Huang, H. M. Catal. Sci. Technol. 2012, 2, 1099. (f) Tang, B. X.; Fang, X. N.; Kuang, R. Y.; Zhou, X. C. Chin. J. Org. Chem. 2013, 33, 319 (in Chinese). (唐伯孝, 方小牛, 匡仁云, 周小春, 有机化学, 2013, 33, 319.)(g) Yang, J.; Deng, M. Z.; Yu, T. Chin. J. Org. Chem. 2013, 33, 693 (in Chinese). (杨军, 邓敏智, 于涛, 有机化学, 2013, 33, 693.)(h) Bian, D. Q.; Nie, Y.; Miao, J. L.; Wang, Y. F.; Zhang, Z. W. Chin. J. Org. Chem. 2013, 33, 1774 (in Chinese). (卞德乾, 聂永, 苗金玲, 王亚峰, 张振伟, 有机化学, 2013, 33, 1774.)(i) Jin, L. Q.; Luo, X. C.; Lei, A. W. Acta Chim. Sinica 2012, 70, 1538 (in Chinese). (靳立群, 罗贤才, 雷爱文, 化学学报, 2012, 70, 1538.)(j) Wen, Y. M.; Jiang, H. F. Acta Chim. Sinica 2012, 70, 1716 (in Chinese). (温燕梅, 江焕峰, 化学学报, 2012, 70, 1716.)
[5] (a) Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242. (b) Li, Z.; Li, C. J. In New Frontiers in Asymmetric Catalysis, Eds.: Mikami, K.; Lautens, M., Wiley, Hoboken, New Jersey, 2007, p. 129.
[6] Li, C. J. Acc. Chem. Res. 2009, 42, 335.
[7] (a) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672. (b) Basle, C.; Li, C. J. Green Chem. 2007, 9, 1047. (c) Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Fares, C.; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106. (d) Xiao, T. B.; Li, L. Y.; Lin, G. L.; Mao, Z. W.; Zhou, L. Org. Lett. 2014, 16, 4232. (e) Zheng, Z. S.; Dian, L. Y.; Yuan, Y. C.; Zhang, N. D.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 7451. (f) Han, W.; Ofial, A. R. Chem. Commun. 2009, 5024. (g) Liu, P.; Liu, Y.; Wong, E. L. M.; Xiang, S.; Che, C. M. Chem. Sci. 2011, 2187. (h) Yoo, W. J.; Li, C. J. Top. Curr. Chem. 2009, 292, 281. (i) Rout, S. K.; Guin, S.; Ali, W.; Gogoi, A.; Patel, B. K. Org. Lett. 2014, 16, 3086. (j) Yoo, W. J.; Kobayashi, S. Green Chem. 2014, 16, 2438. (k) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. (l) Liu, C.; Zhang, H.; Shi, W.; Li, A. Chem. Rev. 2011, 111, 1780. (m) Li, B. J.; Shi, Z. J. Chem. Soc. Rev. 2012, 41, 5588.
[8] For selected relevant reviews: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Bentley, K. W. Nat. Prod. Rep. 2001, 18, 148. (c) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341.
[9] Li, Z.; Li, C. J. Org. Lett. 2004, 6, 4997.
[10] Li, Z.; MacLeod, P. D.; Li, C. J. Tetrahedron: Asymmetry 2006, 17, 590.
[11] Guo, C.; Song, J.; Luo, S. W.; Gong, L. Z. Angew. Chem., Int. Ed. 2010, 49, 5558.
[12] Zhang, G.; Zhang, Y. H.; Wang, R. Angew. Chem. 2011, 123, 10613.
[13] Zhang, J. M.; Tiwari, B.; Xing, C.; Chen, X. K.; Chi, Y. R. Angew. Chem., Int. Ed. 2012, 51, 3649.
[14] Zhang, G.; Ma, Y. X.; Wang, S. L.; Zhang, Y. H.; Wang, R. J. Am. Chem. Soc. 2012, 134, 12334.
[15] Sasamoto, N.; Dubs, C.; Hamashima, Y.; Sodeoka, M. J. Am. Chem. Soc. 2006, 128, 14010.
[16] Zhou, S. B.; Wang, J.; Lin, D. Z.; Zhao, F.; Liu, H. J. Org. Chem. 2013, 78, 11204.
[17] Cao, W. D.; Liu, X. H.; Peng, R. X.; He, P.; Lin, L. L.; Feng, X. M. Chem. Commun. 2013, 49, 3470.

过渡金属催化的不对称交叉脱氢偶联反应研究进展

Asymmetric Catalytic Carbon-Carbon Coupling Reactions via Cross-Dehydrogenative Coupling Reactions

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[3]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[4]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[7]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[8]	Siqiang Fang, Zanjiao Liu, Tianli Wang. Recent Advances of the Atherton-Todd Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1069-1083.
[9]	Xin Kuang, Changhua Ding, Yichen Wu, Peng Wang. Catalytic Enantioselective Preparation of Chiral Allylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3367-3387.
[10]	Yan Zeng, Fei Ye. Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3388-3413.
[11]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[12]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.
[13]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[14]	Dongping Xu, Fei Huang, Lin Tang, Xinming Zhang, Wu Zhang. Visible Light-Induced Hydroxyalkylation of Heteroarenes with Aliphatic Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1493-1500.
[15]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.