Synthesis of 1,1-Diboron Alkanes via Diborylation of Unactivated Primary C(sp3)—H Bonds Enabled by AsPh3/Iridium Catalysis

doi:10.6023/cjoc202111032

Abstract

The AsPh₃/iridium catalyzed diborylation of unactivated primary C(sp³)—H bonds using pyrazoles as directing groups was disclosed. This method could tolerate a variety of functional groups, affording a vast array of 1,1-diboron alkanes in moderate to good yields. The synthetic utility of the current method on a gram-scale reaction for further functionalization was also demonstrated.

Key words: C—H borylation, organoboron, synthetic methods, iridium

Cite this article

Wenqi Liu, Zhenlu Shen, Senmiao Xu. Synthesis of 1,1-Diboron Alkanes via Diborylation of Unactivated Primary C(sp³)—H Bonds Enabled by AsPh₃/Iridium Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1101-1110.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 27

[1]	(a) Hall, D. T. Boronic Acids, Wiley-VCH, Weinheim, 2011.
	(b) Zou, C.; Niu, C.; Liu, X.; Zhang, C. Chin. J. Org. Chem. 2021, 41, 4240. (in Chinese) doi: 10.6023/cjoc202105058
	( 邹辰晨, 牛长浩, 刘新宇, 张淳, 有机化学, 2021, 41, 4240.)
[2]	(a) Wu, C.; Wang, J. Tetrahedron Lett. 2018, 59, 2128. doi: 10.1016/j.tetlet.2018.04.061 pmid: 29379940
	(b) Nallagonda, R.; Padala, K.; Masarwa, A. Org. Biomol. Chem. 2018, 16, 1050. doi: 10.1039/c7ob02978k pmid: 29379940
	(c) Jo, W.; Lee, J. H.; Cho, S. H. Chem. Commun. 2021, 57, 4346. doi: 10.1039/D1CC01048D pmid: 29379940
	(d) Zhang, C.; Hu, W.; Morken, J. P. ACS Catal. 2021, 11, 10660. doi: 10.1021/acscatal.1c02496 pmid: 29379940
[3]	(a) Sun, W.; Wang, L.; Xia, C.; Liu, C. Angew. Chem., nt. Ed. 2018, 57, 5501.
	(b) Li, X.; Hall, D. G. Angew. Chem., nt. Ed. 2018, 57, 10304.
	(c) Iacono, C. E.; Stephens, T. C.; Rajan, T. S.; Pattison, G. J. Am. Chem. Soc. 2018, 140, 2036. doi: 10.1021/jacs.7b12941
	(d) Zheng, P.; Zhai, Y.; Zhao, X.; Xu, T. Chem. Commun. 2018, 54, 13375. doi: 10.1039/C8CC07781A
	(e) Gava, R.; Fernández, E. Chem.-Eur. J. 2019, 25, 8013.
	(f) Lee, B.; Chirik, P. J. J. Am. Chem. Soc. 2020, 142, 2429. doi: 10.1021/jacs.9b11944
	(g) Kuang, Z.; Yang, K.; Zhou, Y.; Song, Q. Chem. Commun. 2020, 56(48), 6469. doi: 10.1039/D0CC00614A
	(h) Li, X.; Hall, D. G. J. Am. Chem. Soc. 2020, 142, 9063. doi: 10.1021/jacs.0c03207
	(i) Zou, L.-H.; Fan, M.; Wang, L.; Liu, C. Chin. Chem. Lett. 2020, 31, 1911. doi: 10.1016/j.cclet.2019.12.016
[4]	(a) Harris, M. R.; Wisniewska, H. M.; Jiao, W.; Wang, X.; Bradow, J. N. Org. Lett. 2018, 20, 2867. doi: 10.1021/acs.orglett.8b00899 pmid: 31184168
	(b) Murray, S. A.; Luc, E. C. M.; Meek, S. J. Org. Lett. 2018, 20, 469. doi: 10.1021/acs.orglett.7b03853 pmid: 31184168
	(c) Lee, H.; Lee, Y.; Cho, S. H. Org. Lett. 2019, 21, 5912. doi: 10.1021/acs.orglett.9b02050 pmid: 31184168
	(d) Kim, J.; Shin, M.; Cho, S. H. ACS Catal. 2019, 9, 8503. doi: 10.1021/acscatal.9b02931 pmid: 31184168
	(e) Kim, J.; Hwang, C.; Kim, Y.; Cho, S. H. Org. Process Res. Dev. 2019, 23, 1663. doi: 10.1021/acs.oprd.9b00179 pmid: 31184168
	(f) Nishino, S.; Hirano, K.; Miura, M. Org. Lett. 2019, 21, 4759. doi: 10.1021/acs.orglett.9b01640 pmid: 31184168
	(g) Shin, M.; Kim, M.; Hwang, C.; Lee, H.; Kwon, H.; Park, J.; Lee, E.; Cho, S. H. Org. Lett. 2020, 22, 2476. doi: 10.1021/acs.orglett.0c00721 pmid: 31184168
	(h) Green, J. C.; Zanghi, J. M.; Meek, S. J. J. Am. Chem. Soc. 2020, 142, 1704. doi: 10.1021/jacs.9b11529 pmid: 31184168
	(i) Zhang, C.; Wu, X.; Wang, C.; Zhang, C.; Qu, J.; Chen, Y. Org. Lett. 2020, 22, 6376. doi: 10.1021/acs.orglett.0c02211 pmid: 31184168
	(j) Kim, M.; Park, B.; Shin, M.; Kim, S.; Kim, J.; Baik, M.-H.; Cho, S. H. J. Am. Chem. Soc. 2021, 143, 1069. doi: 10.1021/jacs.0c11750 pmid: 31184168
	(k) Li, X.; Gao, G.; He, S.; Song, Q. Org. Chem. Front. 2021, 8, 4543. doi: 10.1039/D1QO00632K pmid: 31184168
[5]	(a) Namirembe, S.; Gao, C.; Wexler, R. P.; Morken, J. P. Org. Lett. 2019, 21, 4392. doi: 10.1021/acs.orglett.9b01663 pmid: 31140815
	(b) Kovalenko, M.; Yarmoliuk, D. V.; Serhiichuk, D.; Chernenko, D.; Smyrnov, V.; Breslavskyi, A.; Hryshchuk, O. V.; Kleban, I.; Rassukana, Y.; Tymtsunik, A. V.; Tolmachev, A. A.; Kuchkovska, Y. O.; Grygorenko, O. O. Eur. J. Org. Chem. 2019, 5624. pmid: 31140815
	(c) Sun, W.; Wang, L.; Hu, Y.; Wu, X.; Xia, C.; Liu, C. Nat. Commun. 2020, 11, 3113. doi: 10.1038/s41467-020-16948-5 pmid: 31140815
[6]	Wu, C.; Bao, Z.; Dou, B.; Wang, J. Chem.-Eur. J. 2021, 27, 2294.
[7]	Kumar, N.; Reddy, R. R.; Masarwa, A. Chem.-Eur. J. 2019, 25, 8008.
[8]	(a) Masaki, S.; Michael, S.; Ikuhiro, N.; Katsuhiro, S.; Takuya, K.; Tamejiro, H. Chem. Lett. 2006, 35, 1222. doi: 10.1246/cl.2006.1222
	(b) Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890. doi: 10.1021/ol203413w
	(c) Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang, J.; Liu, J.-H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew. Chem., nt. Ed. 2012, 51, 528.
	(d) Atack, T. C.; Cook, S. P. J. Am. Chem. Soc. 2016, 138, 6139. doi: 10.1021/jacs.6b03157
[9]	(a) Abu Ali, H.; Goldberg, I.; Kaufmann, D.; Burmeister, C.; Srebnik, M. Organometallics 2002, 21, 1870. doi: 10.1021/om011012b pmid: 26264986
	(b) Li, H.; Shangguan, X.; Zhang, Z.; Huang, S.; Zhang, Y.; Wang, J. Org. Lett. 2014, 16, 448. doi: 10.1021/ol403338s pmid: 26264986
	(c) Wommack, A. J.; Kingsbury, J. S. Tetrahedron Lett. 2014, 55, 3163. doi: 10.1016/j.tetlet.2014.03.135 pmid: 26264986
	(d) Cuenca, A. B.; Cid, J.; García-López, D.; Carbó, J. J.; Fernández, E. Org. Biomol. Chem. 2015, 13, 9659. doi: 10.1039/c5ob01523e pmid: 26264986
[10]	Eichhorn, A. F.; Kuehn, L.; Marder, T. B.; Radius, U. Chem. Commun. 2017, 53, 11694. doi: 10.1039/C7CC06302D
[11]	Zhao, H.; Tong, M.; Wang, H.; Xu, S. Org. Biomol. Chem. 2017, 15, 3418. doi: 10.1039/C7OB00654C
[12]	(a) Wang, L.; Zhang, T.; Sun, W.; He, Z.; Xia, C.; Lan, Y.; Liu, C. J. Am. Chem. Soc. 2017, 139, 5257. doi: 10.1021/jacs.7b02518 pmid: 28306251
	(b) He, Z.; Zhu, Q.; Hu, X.; Wang, L.; Xia, C.; Liu, C. Org. Chem. Front. 2019, 6, 900. doi: 10.1039/C9QO00007K pmid: 28306251
	(c) He, Z.; Fan, M.; Xu, J.; Hu, Y.; Wang, L.; Wu, X.; Xia, C.; Liu, C. Chin. J. Org. Chem. 2019, 39, 3438. (in Chinese) doi: 10.6023/cjoc201909008 pmid: 28306251
	( 何泽瑜, 范敏, 徐佳能, 胡越, 王露, 吴旭东, 夏春谷, 刘超, 有机化学, 2019, 39, 3438.) pmid: 28306251
	(d) Li, J.; Wang, H.; Qiu, Z.; Huang, C.-Y.; Li, C.-J. J. Am. Chem. Soc. 2020, 142, 13011. doi: 10.1021/jacs.0c03813 pmid: 28306251
[13]	(a) Li, L.; Gong, T.; Lu, X.; Xiao, B.; Fu, Y. Angew. Chem. Int. Ed. 2018, 57, 12935. doi: 10.1002/anie.201805705
	(b) Teo, W. J.; Ge, S. Angew. Chem. Int. Ed. 2018, 57, 1654. doi: 10.1002/anie.201710389
	(c) Wang, X.; Cui, X.; Li, S.; Wang, Y.; Xia, C.; Jiao, H.; Wu, L. Angew. Chem. Int. Ed. 2020, 59, 13608. doi: 10.1002/anie.202002642
	(d) Jin. S.; Liu, K.; Wang, S.; Song, Q. J. Am. Chem. Soc. 2021, 143, 13124. doi: 10.1021/jacs.1c04248
[14]	(a) Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 291. doi: 10.1021/ja00978a022 pmid: 28199104
	(b) Brown, H. C.; Rhodes, S. P. J. Am. Chem. Soc. 1969, 91, 4306. doi: 10.1021/ja01043a059 pmid: 28199104
	(c) Brown, H. C.; Scouten, C. G.; Liotta, R. J. Am. Chem. Soc. 1979, 101, 96. doi: 10.1021/ja00495a016 pmid: 28199104
	(d) Soundararajan, R.; Matteson, D. S. Organometallics 1995, 14, 4157. doi: 10.1021/om00009a018 pmid: 28199104
	(e) Endo, K.; Hirokami, M.; Shibata, T. Synlett 2009, 1331. pmid: 28199104
	(f) Lee, S.; Li, D.; Yun, J. Chem.-Asian J. 2014, 9, 2440. pmid: 28199104
	(f) Zuo, Z.; Huang, Z. Org. Chem. Front. 2016, 3, 434. doi: 10.1039/C5QO00426H pmid: 28199104
	(g) Krautwald, S.; Bezdek, M. J.; Chirik, P. J. J. Am. Chem. Soc. 2017, 139, 3868. doi: 10.1021/jacs.7b00445 pmid: 28199104
	(h) Gao, G.; Yan, J.; Yang, K.; Chen, F.; Song, Q. Green Chem. 2017, 19, 3997. doi: 10.1039/C7GC01161J pmid: 28199104
	(i) Gao, G.; Kuang, Z.; Song, Q. Org. Chem. Front. 2018, 5, 2249. doi: 10.1039/C8QO00513C pmid: 28199104
	(j) Docherty, J. H.; Nicholson, K.; Dominey, A. P.; Thomas, S. P. ACS Catal. 2020, 10, 4686. doi: 10.1021/acscatal.0c00869 pmid: 28199104
[15]	(a) Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894. doi: 10.1038/nchem.1150 pmid: 26010715
	(b) Feng, X.; Jeon, H.; Yun, J. Angew. Chem. Int. Ed. 2013, 52, 3989. doi: 10.1002/anie.201208610 pmid: 26010715
	(c) Nguyen, P.; Coapes, R. B.; Woodward, A. D.; Taylor, N. J.; Burke, J. M.; Howard, J. A. K.; Marder, T. B. J. Organometallic Chem. 2002, 652, 77. pmid: 26010715
	(d) Coombs, J. R.; Zhang, L.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 16140. doi: 10.1021/ja510081r pmid: 26010715
	(e) Scheuermann, M. L.; Johnson, E. J.; Chirik, P. J. Org. Lett. 2015, 17, 2716. doi: 10.1021/acs.orglett.5b01135 pmid: 26010715
[16]	(a) Hu, J.; Zhao, Y.; Shi, Z. Nat. Catal. 2018, 1, 860. doi: 10.1038/s41929-018-0147-9
	(b) Zhang, L.; Si, X.; Rominger, F.; Hashmi, A. S. K. J. Am. Chem. Soc. 2020, 142, 10485. doi: 10.1021/jacs.0c03197
	(c) Hu, M.; Ge, S. Nat. Commun. 2020, 11, 765. doi: 10.1038/s41467-020-14543-2
	(d) Xu, J.-X.; Wu, F.-P.; Wu, X.-F. Catal. Commun. 2021, 149, 106205. doi: 10.1016/j.catcom.2020.106205
[17]	Cho, S. H.; Hartwig, J. F. Chem. Sci. 2014, 5, 694. doi: 10.1039/C3SC52824C
[18]	Palmer, W. N.; Obligacion, J. V.; Pappas, I.; Chirik, P. J. J. Am. Chem. Soc. 2016, 138, 766. doi: 10.1021/jacs.5b12249 pmid: 26714178
[19]	Palmer, W. N.; Zarate, C.; Chirik, P. J. J. Am. Chem. Soc. 2017, 139, 2589. doi: 10.1021/jacs.6b12896 pmid: 28156108
[20]	Yamamoto, T.; Ishibashi, A.; Suginome, M. Org. Lett. 2019, 21, 6235. doi: 10.1021/acs.orglett.9b02112 pmid: 31386387
[21]	(a) Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992. doi: 10.1039/c0cs00156b pmid: 24553599
	(b) Ros, A.; Fernandez, R.; Lassaletta, J. M. Chem. Soc. Rev. 2014, 43, 3229. doi: 10.1039/c3cs60418g pmid: 24553599
	(c) Kuroda, Y.; Nakao, Y. Chem. Lett. 2019, 48, 1092. doi: 10.1246/cl.190372 pmid: 24553599
	(d) Wright, J. S.; Scott, P. J. H.; Steel, P. G. Angew. Chem. Int. Ed. 2021, 60, 2796. doi: 10.1002/anie.202001520 pmid: 24553599
	(e) Zou, X.; Xu, S. Chin. J. Org. Chem. 2021, 41, 2610. (in Chinese) doi: 10.6023/cjoc202103020 pmid: 24553599
	( 邹晓亮, 徐森苗, 有机化学, 2021, 41, 2610.) pmid: 24553599
[22]	(a) Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 12422. doi: 10.1021/ja305596v pmid: 23398347
	(b) Kawamorita, S.; Miyazaki, T.; Iwai, T.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 12924. doi: 10.1021/ja305694r pmid: 23398347
	(c) Kawamorita, S.; Murakami, R.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2013, 135, 2947. doi: 10.1021/ja3126239 pmid: 23398347
	(d) Cho, S. H.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 8157. doi: 10.1021/ja403462b pmid: 23398347
	(e) Larsen, M. A.; Cho, S. H.; Hartwig, J. J. Am. Chem. Soc. 2016, 138, 762. doi: 10.1021/jacs.5b12153 pmid: 23398347
	(f) Reyes, R. L.; Iwai, T.; Maeda, S.; Sawamura, M. J. Am. Chem. Soc. 2019, 141, 6817. doi: 10.1021/jacs.9b01952 pmid: 23398347
	(g) Reyes, R. L.; Sato, M.; Iwai, T.; Sawamura, M. J. Am. Chem. Soc. 2020, 142, 589. doi: 10.1021/jacs.9b12013 pmid: 23398347
	(h) Reyes, R. L.; Sato, M.; Iwai, T.; Suzuki, K.; Maeda, S.; Sawamura, M. Science 2020, 369, 970. doi: 10.1126/science.abc8320 pmid: 23398347
	(i) Yang, Y.; Chen, L.; Xu, S. Angew. Chem. Int. Ed. 2021, 60, 3524. doi: 10.1002/anie.202013568 pmid: 23398347
	(j) Du, R.; Liu, L.; Xu, S. Angew. Chem. Int. Ed. 2021, 60, 5843. doi: 10.1002/anie.202016009 pmid: 23398347
	(k) Liu, L.; Du, R.; Xu, S. Chin. J. Org. Chem. 2021, 41, 1572. (in Chinese) doi: 10.6023/cjoc202101009 pmid: 23398347
	( 刘路华, 杜荣荣, 徐森苗, 有机化学, 2021, 41, 1572.) pmid: 23398347
[23]	(a) Rablen, P. R.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4648. doi: 10.1021/ja9542451
	(b) Walton, J. C.; McCarroll, A. J.; Chen, Q.; Carboni, B.; Nziengui, R. J. Am. Chem. Soc. 2000, 122, 5455. doi: 10.1021/ja9944812
[24]	Sasaki, I.; Taguchi, J.; Hiraki, S.; Ito, H.; Ishiyama, T. Chem.-Eur. J. 2015, 21, 9236.
[25]	Crystallographic data for 18 could be found in the Supporting Information. CCDC 2104779 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
[26]	Jo, W.; Kim, J.; Choi, S.; Cho, S. H. Angew. Chem. Int. Ed. 2016, 55, 9690. doi: 10.1002/anie.201603329
[27]	Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 4651. doi: 10.1021/jo060692v

Entry	Ligand	Solvent	Yield^b/%
1	None	n-Hexane	63
2	P(C₆F₅)₃	n-Hexane	51
3	P(4-CF₃-C₆H₄)₃	n-Hexane	51
4	AsPh₃	n-Hexane	79
5^c	AsPh₃	n-Hexane	Trace
6^d	AsPh₃	n-Hexane	59
7^e	AsPh₃	n-Hexane	57
8^f	AsPh₃	n-Hexane	51
9	AsPh₃	Cyclohexane	82
10	AsPh₃	THF	51
11	AsPh₃	1,4-Dioxane	51

Entry	Ligand	Solvent	Yield^b/%
1	None	n-Hexane	63
2	P(C₆F₅)₃	n-Hexane	51
3	P(4-CF₃-C₆H₄)₃	n-Hexane	51
4	AsPh₃	n-Hexane	79
5^c	AsPh₃	n-Hexane	Trace
6^d	AsPh₃	n-Hexane	59
7^e	AsPh₃	n-Hexane	57
8^f	AsPh₃	n-Hexane	51
9	AsPh₃	Cyclohexane	82
10	AsPh₃	THF	51
11	AsPh₃	1,4-Dioxane	51

三苯基砷/铱催化的非活化一级碳氢键的双硼化反应合成1,1-偕二硼烷

Synthesis of 1,1-Diboron Alkanes via Diborylation of Unactivated Primary C(sp³)—H Bonds Enabled by AsPh₃/Iridium Catalysis

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 27

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Li Guan, Yanyan Zhou, Yongbao Mao, Kaisen Fu, Wenhui Guan, Yile Fu. Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2682-2698.
[2]	Kaichun Liang, Keyan Bai, Lei Dai, Yuan Liu, Zecong Ye, Yanping Huo. Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1799-1807.
[3]	Weina Tian, Liang Xu, Yu Wei, Pengfei Li. Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1792-1798.
[4]	Wang Jiang, Zhuangzhi Shi. Recent Progress in meta-/para-Selective Aromatic C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1691-1705.
[5]	Linlin Du, Hua Zhang. Photochemical and Electrochemical Borylation Involving Aryl and Alkyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1726-1741.
[6]	Xiaoyang Xu, Meiyan Liu, Chenglong Li, Xuguang Liu. Recent Advance of 1,2-BN Heteroaromatics in China [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1611-1644.
[7]	Tongchang Fang, Liangxuan Xu, Yucheng Qin, Nanquan Jiang, Chao Liu. A Novel Synthesis of Halogenated gem-Diboron Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 777-780.
[8]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[9]	Xiaoyang Xu, Meiyan Liu, Chenglong Li, Xiaoming Wu, Xuguang Liu. Recent Advance of 1,4-BN Heteroaromatics in China [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3826-3843.
[10]	Liqin Cao, Xiaoqin Yang, Maoqiu Li, Lin Liu, Junting Yu, Hua Tan. Synthesis and Electroluminescence Properties of Donor-Acceptor (D-A) Type Near-Infrared Iridium(III) Complex Luminescent Materials with Bipolar Transmission Features [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1831-1838.
[11]	Fei Nie, Guanbo Huang, Lei Dai, Shaofu Chen, Shaomin Ji, Jiaxiong Chen, Yanping Huo. Synthesis and Electroluminescent Properties of Red-Emitting Iridium Complexes Based on Benzofuran-Isoquinoline [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1423-1430.
[12]	Miaomiao Zhang, Bo Han, Haojie Ma, Liang Zhao, Jijiang Wang, Yuqi Zhang. Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1170-1178.
[13]	Siyi Ding, Weisai Zu, Zongcheng Miao, Liang Xu. Synthetic and Computational Study of Four-Coordinate B,B-Diaryl 8-Aminoquinolate Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 812-818.
[14]	Jiahao Li, Hongqiang Liu, Bo Zhang, Bingyang Ge, Dawei Wang. Synthesis of Supported Indazolyl-Pyridyl-Quinoline Iridium Catalyst and Its Application to N-Alkylation of 2-Aminobenzothiazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 619-630.
[15]	Houxiang Lu, Bijie Li. Transition Metal Catalyzed Asymmetric Hydroboration of Internal Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3167-3182.