Recent Progress in meta-/para-Selective Aromatic C—H Borylation

doi:10.6023/cjoc202302022

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1691-1705.DOI: 10.6023/cjoc202302022 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

REVIEWS

芳烃间/对位选择性碳氢硼化反应研究进展

蒋旺^a^,^b, 史壮志^a^,^*()

a 南京大学化学化工学院配位化学国家重点实验室南京 210000
b 扬州大学化学化工学院江苏扬州 225000

收稿日期:2023-02-22 修回日期:2023-04-25 发布日期:2023-05-05
通讯作者: 史壮志
基金资助:
国家自然科学基金(22025104); 国家自然科学基金(22171134); 国家自然科学基金(21972064); 国家自然科学基金(21901111)

Recent Progress in meta-/para-Selective Aromatic C—H Borylation

Wang Jiang^a^,^b, Zhuangzhi Shi^a()

a State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
b College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225000

Received:2023-02-22 Revised:2023-04-25 Published:2023-05-05
Contact: Zhuangzhi Shi
Supported by:
National Natural Science Foundation of China(22025104); National Natural Science Foundation of China(22171134); National Natural Science Foundation of China(21972064); National Natural Science Foundation of China(21901111)

Organoboron compounds are important building blocks to create molecular diversity. Strategies that can transform the readily available hydrocarbons into these compounds by C—H borylation are highly attractive. In this context, significant progress has been made towards iridium-catalyzed C—H borylation. Because substituted arenes typically contain ortho-, meta- and para-C—H bonds, regiocontrol has been a long-standing challenge within this type of chemistry. During the past decade, significant progress has been made in the ortho-selective C—H borylation, while the meta-/para-selectivity is still challenging. This review aims to provide a comprehensive overview of this topic on meta-/para-selective aromatic C—H borylation by iridium catalysis. This topic is categorized into directed and non-directed C—H borylation.

Key words: meta selectivity, para selectivity, iridium catalysis, C—H borylation, directing groups

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 19

Scheme 1. General strategies for meta- and para-selective C—H borylation of arenes

Scheme 2. meta-Selective C—H borylation of aromatic amides via hydrogen bonds

Scheme 3. meta-Selective C—H borylation of benzylic amines/phenylethylamine/amphetamine via hydrogen bonds

Scheme 4. Asymmetric meta-selective C—H borylation of benzylic amines via hydrogen bonds

Scheme 5. Computationally designed ligands enable tunable borylation of remote C—H bonds in arenes

Scheme 6. Controlled meta-/para-selective C—H borylation of aryl sulfonyl compounds via hydrogen bonds

Scheme 7. meta-Selective C—H borylation of acyl aromatic amines via electrostatic interactions

Scheme 8. meta-Selective C—H borylation of aromatic aldehyde via B—N coordination

Scheme 9. meta-Selective C—H borylation of pyridines via coordination

Scheme 10. Ion-pair assisted meta-selective C—H borylation

Scheme 11. meta-/para-Selective C—H borylation of aromatic amide/aromatic esters

Scheme 12. meta-Selective borylation of amide and pyridine

Scheme 13. Ion-pair assisted meta-selective C—H borylation aromatic quaternary ammonium salt

Scheme 14. para-Selective borylation of aromatics by diphosphate ligands

Scheme 15. meta-Selective borylation of aromatic hydrocarbons

Scheme 16. para-Selective borylation of N-Boc amide

Scheme 17. para-Selective borylation assisted by aluminum lewis acid

Scheme 18. Ion-pair assisted para-selective borylation

Scheme 19. para-Selective borylation of aromatic amines

References 23

[1]	(a) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. doi: 10.1021/cr900184e pmid: 30033454
	(b) Zhang, F.; Spring, D. R. Chem. Soc. Rev. 2014, 43, 6906. doi: 10.1039/C4CS00137K pmid: 30033454
	(c) He, J.; Wasa, M.; Chan, K.S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754. doi: 10.1021/acs.chemrev.6b00622 pmid: 30033454
	(d) Sambiagio, C.; Schönbauer, D.; Blieck, R.; Dao-Huy, T.; Pototschnig, G.; Schaaf, P.; Wiesinger, T.; Zia, M. F.; Wencel-Delord, J.; Besset, T.; Maes, B. U. W.; Schnurch, M. Chem. Soc. Rev. 2018, 47, 6603. doi: 10.1039/c8cs00201k pmid: 30033454
[2]	(a) Kuninobu, Y.; Torigoe, T. Org. Biomol. Chem. 2020, 18, 4126. doi: 10.1039/D0OB00703J
	(b) Haldar, C.; Hoque, M. E.; Chaturvedi, J.; Hassan, M. M. M.; Chattopadhyay, B. Chem. Commun. 2021, 57, 13059. doi: 10.1039/D1CC05104K
	(c) Dutta, U.; Maiti, S.; Bhattacharya, T.; Maiti, D. Science 2021, 372, 701.
	(d) Wang, M.; Shi, Z. Chem. Rev. 2020, 120, 7348. doi: 10.1021/acs.chemrev.9b00384
	(e) Hu, J.; Ferger, M.; Shi, Z.; Marder, T. B. Chem. Soc. Rev. 2021, 50, 13129. doi: 10.1039/D0CS00843E
	(f) Hu, J.; Lv, J.; Shi, Z. Trends Chem. 2022, 4, 685. doi: 10.1016/j.trechm.2022.04.011
[3]	Kuninobu, Y.; Ida, H.; Nishi, M.; Kanai, M. Nat. Chem. 2015, 7, 712. doi: 10.1038/nchem.2322
[4]	Davis, H. J.; Genov, G. R.; Phipps, R. J. Angew. Chem., Int. Ed. 2017, 56, 13351. doi: 10.1002/anie.201708967
[5]	Genov, G. R.; Douthwaite, J. L.; Lahdenperä, A. S. K.; Gibson, D. C.; Phipps, R. J. Science 2020, 367, 1246. doi: 10.1126/science.aba1120
[6]	Chang, W.; Chen, Y.; Lu, S.; Jiao, H.; Wang, Y.; Zheng, T.; Shi, Z.; Han, Y.; Lu, Y.; Wang, Y.; Pan, Y.; Yu, J.; Houk, K. N.; Liu, F.; Liang, Y. Chem 2022, 8, 1775. doi: 10.1016/j.chempr.2022.04.025
[7]	Wang, Y.; Chang, W.; Qin, S.; Ang, H.; Ma, J.; Lu, S.; Liang, Y. Angew. Chem., Int. Ed. 2022, 61, e202206797.
[8]	Chaturvedi, J.; Haldar, C.; Bisht, R.; Pandey, G.; Chattopadhyay, B. J. Am. Chem. Soc. 2021, 143, 7604. doi: 10.1021/jacs.1c01770 pmid: 33988369
[9]	Bisht, R.; Chattopadhyay, B. J. Am. Chem. Soc. 2016, 138, 1, 84. doi: 10.1021/jacs.5b11683
[10]	Trouv, J.; Zardi, P.; Al-Shehimy, S.; Roisnel, T.; Doria, R. G. Angew. Chem., Int. Ed. 2021, 60, 18006. doi: 10.1002/anie.v60.33
[11]	Davis, H. J.; Mihai, M. T.; Phipps, R. J. J. Am. Chem. Soc. 2016, 138, 39, 12759. doi: 10.1021/jacs.6b08164
[12]	(a) Hoque, M. E.; Bisht, R.; Haldar, C.; Chattopadhyay, B. J. Am. Chem. Soc. 2017, 139, 7745. doi: 10.1021/jacs.7b04490
	(b) Bisht, R.; Hoque, M. E.; Chattopadhyay, B. Angew. Chem., Int. Ed. 2018, 57, 15762. doi: 10.1002/anie.201809929
[13]	Yang, L. C.; Uemura, N.; Nakao, Y. J. Am. Chem. Soc. 2019, 141, 7972. doi: 10.1021/jacs.9b03138
[14]	Lu, S.; Zheng, T. Y.; Ma, J. W.; Deng, Z. M.; Qin, S. M.; Chen, Y.; Liang, Y. Angew. Chem., Int. Ed. 2022, 61, e202201285.
[15]	Saito, Y.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2015, 137, 5193. doi: 10.1021/jacs.5b02052
[16]	Ramadoss, B.; Jin, Y.; Asako, S.; Ilies, L. Science 2022, 375, 658. doi: 10.1126/science.abm7599
[17]	Hoque, M. E.; Bisht, R.; Unnikrishnan, A.; Dey, S.; Hassan, M. M. M.; Guria, S.; Rai, R. N.; Sunoj, R. B.; Chattopadhyay, B. Angew. Chem., Int. Ed. 2022, 61, e202203539.
[18]	Yang, L.; Semba, K.; Nakao, Y. Angew. Chem., Int. Ed. 2017, 56, 4853. doi: 10.1002/anie.v56.17
[19]	Mihai, M. T.; Williams, B. D.; Phipps, R. J. J. Am. Chem. Soc. 2019, 141, 15477. doi: 10.1021/jacs.9b07267
[20]	Bastidas, J. R. M.; Oleskey, T. J.; Miller, S. L.; Smith III, M. R.; Maleczka, R. E. J. Am. Chem. Soc. 2019, 141, 15483. doi: 10.1021/jacs.9b08464 pmid: 31525037
[21]	Haldar, C.; Bisht, R.; Chaturvedi, J.; Guria, S.; Hassan, M. M. M.; Ram, B.; Chattopadhyay, B. Org. Lett. 2022, 24, 8147. doi: 10.1021/acs.orglett.2c03188
[22]	(a) Gao, P.; Yuan, C.; Zhao, Y.; Shi, Z. Chem 2018. 4, 2201. doi: 10.1016/j.chempr.2018.07.003 pmid: 30370972
	(b) Wang, D.; Xue, X.; Houk, K. N.; Shi, Z. Angew. Chem., Int. Ed. 2018, 57, 16861. doi: 10.1002/anie.201811036 pmid: 30370972
[23]	(a) Lv, J.; Chen, X.; Xue, X.; Zhao, B.; Liang, Y.; Wang, M.; Jin, L.; Yuan, Y.; Han, Y.; Zhao, Y.; Lu, Y.; Zhao, J.; Sun, W.; Houk, K. N.; Shi, Z. Nature 2019, 575, 336. doi: 10.1038/s41586-019-1640-2
	(b) Iqbal, S. A.; Cid, J.; Procter, R. J.; Uzelac, M.; Yuan, K.; Ingleson, M. J. Angew. Chem., Int. Ed. 2019, 58, 15381. doi: 10.1002/anie.v58.43
	(c) Yamazaki, K.; Rej, S.; Ano, Y.; Chatani, N. Org. Lett. 2022, 24, 213. doi: 10.1021/acs.orglett.1c03829

芳烃间/对位选择性碳氢硼化反应研究进展

Recent Progress in meta-/para-Selective Aromatic C—H Borylation

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 19

References 23

Related Articles 7

Recommended Articles

Metrics

Comments

[1]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[2]	Fangfang Song, Shiyang Zhu, Hao Wang, Gong Chen. Iridium-Catalyzed Intermolecular N—N Coupling for Hydrazide Synthesis Using N-Benzoyloxycarbamates as Acyl Nitrene Precursor [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4050-4058.
[3]	Wu Yongjie, Shi Bingfeng. Transition Metal-Catalyzed C-H Activation via Imine-Based Transient Directing Group Strategy [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3517-3535.
[4]	Huang Fangsheng, Chen Xun, Xie Ying, Zeng Wei. Progress in the Transition Metal-Catalyzed C(sp²)-H Bond Functionalization of Azoarenes [J]. Chin. J. Org. Chem., 2017, 37(1): 31-39.
[5]	He Jiangqi, Lou Shaojie, Xu Danqian. Recent Advances in Transition-Metal Catalyzed C—H Bond Fluorination [J]. Chin. J. Org. Chem., 2016, 36(6): 1218-1228.
[6]	Wang Yong, Cheng Guolin, Cui Xiuling. Easily Modified Directing Groups for the Palladium-Catalyzed C—H Functionalization [J]. Chin. J. Org. Chem., 2012, 32(11): 2018-2039.
[7]	BIAN Hong-Xu, YANG Ding-Qiao. Progress of Iridium-Catalyzed Cycloaddition Reactions [J]. Chin. J. Org. Chem., 2010, 30(04): 506-514.