Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids

doi:10.6023/cjoc202110042

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1198-1209.DOI: 10.6023/cjoc202110042 Previous Articles Next Articles

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镍催化丁二烯、亚胺和烯基硼酸的三组分偶联反应

张玉荣^a^,^b, 王晗^a^,^*(), 茆勇军^a, 施世良^a^,^b^,^*()

a 上海工程技术大学化学化工学院上海 201620
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:2021-10-29 修回日期:2021-11-28 发布日期:2021-12-02
通讯作者: 王晗, 施世良
基金资助:
国家自然科学基金(21690074); 国家自然科学基金(21871288); 国家自然科学基金(91856111); 国家自然科学基金(21821002); 国家自然科学基金(22171280); 中国科学院战略性先导科技专项(XDB20000000)

Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids

Yurong Zhang^a^,^b, Han Wang^a(), Yongjun Mao^a, Shiliang Shi^a^,^b()

a College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032

Received:2021-10-29 Revised:2021-11-28 Published:2021-12-02
Contact: Han Wang, Shiliang Shi
Supported by:
National Natural Science Foundation of China(21690074); National Natural Science Foundation of China(21871288); National Natural Science Foundation of China(91856111); National Natural Science Foundation of China(21821002); National Natural Science Foundation of China(22171280); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB20000000)

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Abstract

A Ni-catalyzed three-component coupling reaction of alkenylboronic acids, aldimines, and 1,3-butadiene for rapid synthesis of homoallylic amines bearing a skipped diene moiety is disclosed. This reaction represents a rare example for modular 1,4-dicarbofunctionalization of 1,3-butadiene, an abundant feedstock chemical. This protocol furnishes a diverse variety of (E)-homoallylic amines in high yields with excellent regio- and stereo-selectivity. The mild and base-free reaction condition enables excellent functional group tolerance and broad scope for aldimine and alkenylboronic acid coupling partners.

Key words: skipped diene, nickel catalysis, butadiene, multicomponent reaction, coupling, homoallylic amine

Cite this article

Yurong Zhang, Han Wang, Yongjun Mao, Shiliang Shi. Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1198-1209.

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Fig. & Tab. 7

Scheme 1. Examples of natural products containing homoallylic amines and approaches to homoallylic amines

Scheme 2. Examples of skipped dienes in natural products, and synthetic method to skipped dienes

Table 1. Optimization of the reaction conditions

Table 2. Scope of aldiminesa

Table 3. Scope of organoboronic acids

Scheme 3. Gram-scale reaction, tandem coupling-lactamization, and isoprene-imine coupling

Scheme 4. Proposed catalytic cycle

References 20

[1]	(a) Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications, Wiley-VCH, Weinheim, 2010.
	(b) Lawrence, S. A. Amines: Synthesis, Properties and Applications, Cambridge University Press, Cambridge, U. K., 2004.
	(c) Puentes, C. O.; Kouznetsov, V. J. J. Heterocycl. Chem. 2002, 39, 595.
[2]	(a) Yus, M.; Gonzalez-Gomez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774. doi: 10.1021/cr1004474
	(b) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595. doi: 10.1021/cr400008h
	(c) Huo, H.-X.; Duvall, J. R.; Huang, M.-Y.; Hong, R. Org. Chem. Front. 2014, 1, 303. doi: 10.1039/C3QO00081H
[3]	(a) Dahlmann, M.; Grub, J.; Löser, E. Butadiene, Wiley-VCH, Weinheim, Germany, 2011.
	(b) Weitz, H. M.; Löser, E. Isoprene, Wiley-VCH, Weinheim, Germany, 2000.
[4]	(a) Wu, Z.; Zhang, W. Chin. J. Org. Chem. 2017, 37, 2250. (in Chinese) doi: 10.6023/cjoc201704031
	( 吴正兴, 张万斌, 有机化学, 2017, 37, 2250.)
	(b) Xiong, Y.; Sun, Y.-W.; Zhang, G.-Z. Tetrahedron Lett. 2018, 59, 347. doi: 10.1016/j.tetlet.2017.12.059
	(c) Holmes, M.; Schwartz, L. A.; Krische, M. J. Chem. Rev. 2018, 118, 6026. doi: 10.1021/acs.chemrev.8b00213
	(d) Wang, P.-S.; Shen, M.-L.; Gong, L.-Z. Synthesis 2018, 50, 956. doi: 10.1055/s-0036-1590986
	(e) Perry, G. J. P.; Jia, T.; Procter, D. J. ACS Catal. 2020, 10, 1485. doi: 10.1021/acscatal.9b04767
	(f) Wang, X.-X.; Lu, X.; Li, Y.; Wang, J.-W.; Fu, Y. Sci. China Chem. 2020, 63, 1586. doi: 10.1007/s11426-020-9838-x
	(g) Zhang, H.; Gu, Q.; You, S.; Chin. J. Org. Chem. 2019, 39, 15. (in Chinese)
	( 张慧君, 顾庆, 游书力, 有机化学, 2019, 39, 15.)
[5]	Kimura, M.; Miyachi, A.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2004, 126, 14360. doi: 10.1021/ja0450354
[6]	(a) Chen, T.-Y.; Tsutsumi, R.; Montgomery, T. P.; Volchkov, I.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 1798. doi: 10.1021/ja5130258
	(b) Schmitt, D. C.; Lee, J.; Dechert-Schmitt, A.-M. R.; Yamaguchi, E.; Krische, M. J. Chem. Commun. 2013, 49, 6096. doi: 10.1039/c3cc43463j
	(c) Zhu, S.; Lu, X.; Luo, Y.; Zhang, W.; Jiang, H.; Yan, M.; Zeng, W. Org. Lett. 2013, 15, 1440. doi: 10.1021/ol4006079
[7]	(a) Li, C.; Liu, R.-Y.; Jesikiewicz, L. T.; Yang, Y.; Liu, P.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 5062. doi: 10.1021/jacs.9b01784
	(b) Jiang, L.; Cao, P.; Wang, M.; Chen, B.; Wang, B.; Liao, J. Angew. Chem., nt. Ed. 2016, 55, 13854.
	(c) Li, M.; Wang, J.; Meng, F. Org. Lett. 2018, 20, 7288. doi: 10.1021/acs.orglett.8b03216
	(d) Fu, B.; Yuan, X.; Li, Y.; Wang, Y.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2019, 21, 3576. doi: 10.1021/acs.orglett.9b00979
	(e) Gui, Y.-Y.; Hu, N.; Chen, X.-W.; Liao, L.-L.; Ju, T.; Ye, J.-H.; Zhang, Z.; Li, J.; Yu, D.-G. J. Am. Chem. Soc. 2017, 139, 17011. doi: 10.1021/jacs.7b10149
[8]	(a) Kojima, K.; Kimura, M.; Tamaru, Y. Chem. Commun. 2005, 4717.
	(b) Kimura, M.; Kojima, K.; Tatsuyama, Y.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 6332. doi: 10.1021/ja0616332
	(c) Kimura, M.; Tatsuyama, Y.; Kojima, K.; Tamaru, Y. Org. Lett. 2007, 9, 1871. doi: 10.1021/ol0703480
[9]	Li, Y.-Q.; Shi, S.-L. Organometallics 2021, 40, 2345. doi: 10.1021/acs.organomet.1c00096
[10]	(a) McCammant, M. S.; Liao, L.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 4167. doi: 10.1021/ja3110544 pmid: 31857484
	(b) Tao, Z.-L.; Adili, A.; Shen, H.-C.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem. Int. Ed. 2016, 55, 4322. doi: 10.1002/anie.201600148 pmid: 31857484
	(c) Tortajada, A.; Ninokata, R.; Martin, R. J. Am. Chem. Soc. 2018, 140, 2050. doi: 10.1021/jacs.7b13220 pmid: 31857484
	(d) Boerth, J. A.; Maity, S.; Williams, S. K.; Mercado, B. Q.; Ellman, J. A. Nat. Catal. 2018, 1, 673. doi: 10.1038/s41929-018-0123-4 pmid: 31857484
	(e) Xiong, Y.; Zhang, G. J. Am. Chem. Soc. 2018, 140, 2735. doi: 10.1021/jacs.7b12760 pmid: 31857484
	(f) Yang, J.; Ji, D.-W.; Hu, Y.-C.; Min, X.-T.; Zhou, X.; Chen, Q.-A. Chem. Sci. 2019, 10, 9560. doi: 10.1039/c9sc03747k pmid: 31857484
	(g) Yang, J.; Liu, J.; Neumann, H.; Franke, R.; Jackstell, R.; Beller, M. Science 2019, 366, 1514. doi: 10.1126/science.aaz1293 pmid: 31857484
	(h) Li, Y.-Q.; Chen, G.; Shi, S.-L. Org. Lett. 2021, 23, 2571. doi: 10.1021/acs.orglett.1c00488 pmid: 31857484
[11]	(a) Denmark, S. E.; Guagnano, V.; Dixon, J. A.; Stolle, A. J. Org. Chem. 1997, 62, 4610. doi: 10.1021/jo970686m
	(b) Lin, H.-C.; Wang, P.-S.; Tao, Z.-L.; Chen, Y.-G.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2016, 138, 14354. doi: 10.1021/jacs.6b08236
	(c) Fan, L.-F.; Luo, S.-W.; Chen, S.-S.; Wang, T.-C.; Wang, P.-S.; Gong, L.-Z. Angew. Chem., nt. Ed. 2019, 58, 16806.
[12]	(a) Shinohara, Y.; Kudo, F.; Eguchit, T. J. Am. Chem. Soc. 2011, 133, 18134. doi: 10.1021/ja208927r pmid: 22010945
	(b) Tang, W.; Prusov, E. V. Angew. Chem., nt. Ed. 2012, 51, 3401. pmid: 22010945
	(c) Winter, P.; Hiller, W.; Christmann, M. Angew. Chem., nt. Ed. 2012, 51, 3396. pmid: 22010945
[13]	(a) Lian, X.; Chen, W.; Dang, L.; Li, Y.; Ho, C.-Y. Angew. Chem., nt. Ed. 2017, 56, 9048.
	(b) Jing, S.-M.; Balasanthiran, V.; Pagar, V.; Gallucci, J. C.; RajanBabu, T.-V. J. Am. Chem. Soc. 2017, 139, 18034. doi: 10.1021/jacs.7b10055
	(c) Schmidt, V.-A.; Kennedy, C.-R.; Bezdek, M.-J.; Chirik, P.-J. J. Am. Chem. Soc. 2018, 140, 3443. doi: 10.1021/jacs.8b00245
	(d) Bohn, M.-A.; Schmidt, A.; Hilt, G.; Dindaroğlu, M.; Schmalz, H.-G. Angew. Chem., nt. Ed. 2011, 50, 9689.
[14]	(a) Kimura, M.; Ezoe, A.; Mori, M.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 201. doi: 10.1021/ja0469030
	(b) Li, Y.-Q.; Shi, S.-L. Chin. J. Org. Chem. 2021, 41, 1939. (in Chinese)
	( 李雨青, 施世良, 有机化学, 2021, 41, 1939.)
[15]	(a) McCammant, M.-S.; Liao, L.; Sigman, M.-S. J. Am. Chem. Soc. 2013, 135, 4167. doi: 10.1021/ja3110544 pmid: 25705367
	(b) McCammant, M.-S.; Sigman, M.-S. Chem. Sci. 2015, 6, 1355. pmid: 25705367
	(c) Wang, C.-G.; Zhang, Y.; Wang, S.; Chen, B.; Li, Y.; Gao, Y.; Hu, P.; Wang, B.-Q.; Cao, P. Org. Lett. 2021, 23, 535. doi: 10.1021/acs.orglett.0c04059 pmid: 25705367
	(d) Pang, X.; Zhao, Z.-Z.; Wei, X.-X.; Qi, L.; Xu, G.-L.; Duan, J.; Liu, X.-Y.; Shu, X.-Z. J. Am. Chem. Soc. 2021, 143, 4536. doi: 10.1021/jacs.1c00142 pmid: 25705367
[16]	(a) Bin, H.-Y.; Wei, X.; Zi, J.; Zuo, Y.-J.; Wang, T.-C.; Zhong, C.-M. ACS Catal. 2015, 5, 6670. doi: 10.1021/acscatal.5b01441
	(b) Xu, G.; Zhao, H.; Fu, B.; Cang, A.; Zhang, G.; Zhang, Q.; Xiong, T.; Zhang, Q. Angew. Chem., nt. Ed. 2017, 56, 13130.
	(c) Song, F.; Wang, F.; Guo, L. Feng, X.; Zhang, Y.; Chu, L. Angew. Chem., nt. Ed. 2020, 59, 177.
	(d) Ma, W.-Y.; Han, G.-Y.; Kang, S.-l.; Pang, X.-B.; Liu, X.-Y.; Shu, X.-Z. J. Am. Chem. Soc. 2021, 143, 15930. doi: 10.1021/jacs.1c08695
[17]	(a) Montgomery, L. Angew. Chem., nt. Ed. 2004, 43, 3890.
	(b) Standley, E.-A.; Tasker, S.-Z.; Jensen, K.-L.; Jamison, T.-F. Acc. Chem. Res. 2015, 48, 1503. doi: 10.1021/acs.accounts.5b00064
	(c) Hoshimoto, Y.; Ohashi, M.; Ogoshi, S. Acc. Chem. Res. 2015, 48, 1746. doi: 10.1021/acs.accounts.5b00061
[18]	(a) Lennox, A.-J.; Lloyd-Jones, G.-C. Angew. Chem., nt. Ed. 2013, 52, 7362. pmid: 27081068
	(b) Carrow, B.-P.; Hartwig, J.-F. J. Am. Chem. Soc. 2011, 133, 2116. doi: 10.1021/ja1108326 pmid: 27081068
	(c) Thomas, A.-A.; Denmark, S.-E. Science 2016, 352, 329. doi: 10.1126/science.aad6981 pmid: 27081068
	(d) Malapit, C. A.; Bour, J. R.; Brigham, C. E.; Sanford, M. S. Nature 2018, 563, 100. doi: 10.1038/s41586-018-0628-7 pmid: 27081068
[19]	Kimura, M.; Matsuo, S.; Shibata, K.; Tamaru, Y. Angew. Chem., nt. Ed. 1999, 38, 3386.
[20]	(a) Zhang, W.-B.; Yang, X.-T.; Ma, J.-B.; Su, Z.-M.; Shi, S.-L. J. Am. Chem. Soc. 2019, 141, 5628. doi: 10.1021/jacs.9b00931
	(b) Cai, Y.; Zhang, J.-W.; Li, F.; Liu, J.-M.; Shi, S.-L. ACS Catal. 2019, 9, 1. doi: 10.1021/acscatal.8b04198
	(c) Cai, Y.; Ye, X.; Liu, S.; Shi, S.-L. Angew. Chem., nt. Ed. 2019, 58, 13433.
	(d) Shen, D.; Zhang, W.-B.; Li, Z.; Shi, S.-L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 1125. doi: 10.1002/adsc.201901582
	(e) Li, Y.-Q.; Li, F.; Shi, S.-L. Chin. J. Chem. 2020, 38, 1035. doi: 10.1002/cjoc.202000019
	(f) Cai, Y.; Ruan, L.-X.; A. Rahman; Shi, S.-L. Angew. Chem., nt. Ed. 2021, 60, 5262.
	(g) Wang, Z.-C.; Gao, J.; Cai, Y.; Ye, X.; Shi, S.-L. CCS Chem. 2021, 3, 1445. doi: 10.31635/ccschem.020.202000356
	(h) Wang, Z.-C.; Xie, P.-P.; Xu, Y.; Hong, X.; Shi, S.-L. Angew. Chem., nt. Ed. 2021, 60, 16077.
	(i) Cai, Y.; Shi, S.-L. J. Am. Chem. Soc. 2021, 143, 11963. doi: 10.1021/jacs.1c06614
	(j) Zhang, W.-B.; Chen, G.; Shi, S.-L. J. Am. Chem. Soc. 2021, 2022, 144, 130. doi: 10.1021/jacs.1c12625

镍催化丁二烯、亚胺和烯基硼酸的三组分偶联反应

Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids

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