Recent Advances in Photoinduced Borylation via N-Heterocyclic Carbene Boryl Radicals

Xu Chen; Xuesi Zhou; Jiawei He; Xiang Liu

doi:10.1055/a-2405-2961

Synthesis, Table of Contents

Synthesis 2025; 57(17): 2539-2550
DOI: 10.1055/a-2405-2961

short review

Boryl Radical Chemistry

Recent Advances in Photoinduced Borylation via N-Heterocyclic Carbene Boryl Radicals

Authors

Xu Chen
Xuesi Zhou
Jiawei He
Xiang Liu∗

Abstract

All articles of this category

Abstract

Organoboron compounds are recognized as essential synthetic intermediates in organic chemistry and have found broad applications in pharmaceutical and materials science. In recent years, the development of novel boronating reagents has opened new avenues for the synthesis of organoboron compounds. Among these, N-heterocyclic carbene boranes (NHC-boranes), with their unique advantages, have garnered sustained interest and have evolved into important precursors for boron-centered radicals, participating in a diverse array of visible-light-induced borylation reactions. This short review primarily focuses on visible-light-induced radical borylation reactions involving NHC-boranes, summarizing the latest advancements in the field and offering inspiration for subsequent research.

1 Introduction

2 Photoinduced Borylation via NHC-Boryl Radicals

2.1 Photoinduced Borylation of Polyfluoroarenes

2.2 Photoinduced Borylation of Arenes

2.3 Photoinduced Borylation of Alkenes

2.4 Photoinduced Borylation of Alkynes

2.5 Photoinduced Borylation of Other Substrates

3 Conclusion and Future Prospects

Key words

photoredox catalysis - N-heterocyclic carbene boranes - radical reaction - borylation - alkenes

Full Text

References

References

1a Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
1b Fyfe JW, Watson AJ. Chem 2017; 3: 31
1c Neeve EC, Geier SJ, Mkhalid IA, Westcott SA, Marder TB. Chem. Rev. 2016; 116: 9091
1d Cuenca AB, Shishido R, Ito H, Fernandez E. Chem. Soc. Rev. 2017; 46: 415
1e Lennox AJ. J, Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412

2a Kim JH, Constantin T, Simonetti M, Llaveria J, Sheikh NS, Leonori D. Nature 2021; 595: 677
2b Yang L, Semba K, Nakao Y. Angew. Chem. Int. Ed. 2017; 56: 4853
2c Yang L, Uemura N, Nakao Y. J. Am. Chem. Soc. 2019; 141: 7972
2d Trouve J, Zardi P, Al-Shehimy S, Roisnel T, Gramage-Doria R. Angew. Chem. Int. Ed. 2021; 60: 18006

3a Takahashi K, Geib SJ, Maeda K, Curran DP, Taniguchi T. Org. Lett. 2021; 23: 1071
3b Jin J.-K, Zhang F.-L, Zhao Q, Lu J.-A, Wang Y.-F. Org. Lett. 2018; 20: 7558
3c Huang Y.-S, Wang J, Zheng W.-X, Zhang F.-L, Yu Y.-J, Zheng M, Zhou X, Wang Y.-F. Chem. Commun. 2019; 55: 11904
3d Shimoi M, Watanabe T, Maeda K, Curran DP, Taniguchi T. Angew. Chem. Int. Ed. 2018; 130: 9629
3e Li G, Huang G, Sun R, Curran D, Dai W. Org. Lett. 2021; 23: 4353
3f Liu Y, Li J.-L, Liu X.-G, Wu J.-Q, Huang Z.-S, Li Q, Wang H. Org. Lett. 2021; 23: 1891
3g Liu X, Lin EE, Chen G, Li J.-L, Liu P, Wang H. Org. Lett. 2019; 21: 8454
3h Wang K, Zhuang Z, Tia H, Wu P, Zhao X, Wang H. Chin. Chem. Lett. 2020; 31: 1564

4a Ye T, Zhang F.-L, Xia H.-M, Zhou X, Yu Z.-X, Wang Y.-F. Nat. Commun. 2022; 13: 426
4b Jian Y, Wen F, Shang J, Li X, Liu Z, An Y, Wang Y. Org. Chem. Front. 2024; 11: 149
4c Pan Q.-J, Miao Y.-Q, Cao H.-J, Liu Z, Chen X. J. Org. Chem. 2024; 89: 5049

5a Wang H, Gao X, Lv Z, Abdelilah T, Lei A. Chem. Rev. 2019; 119: 6769
5b Liu Q, Wu L.-Z. Nat. Sci. Rev. 2017; 4: 359
5c Chen B, Wu L.-Z, Tung C.-H. Acc. Chem. Res. 2018; 51: 2512
5d Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
5e Yu X.-Y, Chen J.-R, Xiao W.-J. Chem. Rev. 2021; 121: 506

Selected reviews:

6a Chan AY, Perry IB, Bissonnette NB, Buksh BF, Edwards GA, Frye LI, Garry OL, Lavagnino MN, Li BX, Liang Y, Mao E, Millet A, Oakley JV, Reed NL, Sakai H, Seath AC. P, MacMillan DW. C. Chem. Rev. 2022; 122: 1485
6b Wang C.-S, Dixneuf PH, Soulé JF. Chem. Rev. 2018; 118: 7532
6c Tay NE. S, Lehnherr D, Rovis T. Chem. Rev. 2022; 122: 2487
6d Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102

7a Taniguchi T. Chem. Soc. Rev. 2021; 50: 8995
7b Peng T.-Y, Zhang F.-L, Wang Y.-F. Acc. Chem. Res. 2023; 56: 169
7c Tian Y.-M, Guo X.-N, Braunschweig H, Radius U, Marder TB. Chem. Rev. 2021; 121: 3561
7d Taniguchi T. Eur. J. Org. Chem. 2019; 6308

8 Xia P.-J, Ye Z.-P, Hu Y.-Z, Xiao J.-A, Chen K, Xiang H.-Y, Chen X.-Q, Yang H. Org. Lett. 2020; 22: 1742
9 Xu W, Jiang H, Leng J, Ong H.-W, Wu J. Angew. Chem. Int. Ed. 2020; 59: 4009
10 Miao Y.-Q, Pan Q.-J, Kang J.-X, Dai X, Liu Z, Chen X. Org. Chem. Front. 2024; 11: 1462
11 Dai W, Geib SJ, Curran DP. J. Am. Chem. Soc. 2020; 142: 6261

12a Starrett J, Montzka T, Crosswell A, Cavanagh R. J. Med. Chem. 1989; 32: 2204
12b Quattrini L, Gelardi EL. M, Coviello V, Sartini SD, Ferraris M, Mori M, Nakano I, Garavaglia S, La Motta C. J. Med. Chem. 2020; 63: 4603
12c Al-Tel TH, Al-Qawasmeh RA, Zaarour R. Eur. J. Med. Chem. 2011; 46: 1874

13a Wang Y, Zheng H, Xu J, Zhuang C, Liu X, Cao H. Org. Chem. Front. 2021; 8: 4706
13b Liu X, Wang Y, Song D, Wang Y, Cao H. Chem. Commun. 2020; 56: 15325
13c Shi X, Wang Q, Tang Z, Huang H, Cao T, Cao H, Liu X. Org. Lett. 2024; 26: 1255
13d Zhu B, Li W, Chen H, Wu M, Hu J, Cao H, Liu X. Adv. Synth. Catal. 2022; 364: 2911
13e Li W, Zhang M, Yan J, Ni L, Cao H, Liu X. Org. Chem. Front. 2022; 9: 2529

14 Zheng H, Lu H, Su C, Yang R, Zhao L, Liu X, Cao H. Chin. J. Chem. 2023; 41: 193

15a Song D, Huang C, Liang P, Zhu B, Liu X, Cao H. Org. Chem. Front. 2021; 8: 2583
15b Zhou J, Shi X, Zheng H, Chen G, Zhang C, Liu X, Cao H. Org. Lett. 2022; 24: 3238
15c Liu X, Song D, Zhang Z, Lin J, Zhuang C, Zhan H, Cao H. Org. Biomol. Chem. 2021; 19: 5284
15d Liu X, Zhou J, Zheng H, Liu J, Liu Z, Ni L, Kong X, Zhang C, Cao H. Chin. J. Chem. 2023; 41: 924
15e Yan J, Zhong S, Chen X, Luo Y, Cao H, Liu X, Zhao L. J. Org. Chem. 2024; 89: 4840
15f Liu X, Shi X, Zhou J, Huang C, Lin Y, Zhang C, Cao H. Chem. Commun. 2023; 59: 4051

16 Zheng H, Xiong H, Su C, Cao H, Yao H, Liu X. RSC Adv. 2022; 12: 470

Selected examples:

17a Wang JZ, Mao E, Nguyen JA, Lyon WL, MacMillan DW. C. J. Am. Chem. Soc. 2024; 146: 15693
17b Boyington AJ, Riu ML. Y, Jui NT. J. Am. Chem. Soc. 2017; 139: 6582
17c Hari DP, Hering T, Konig B. Angew. Chem. Int. Ed. 2014; 53: 725
17d Bunescu A, Abdelhamid Y, Gaunt MJ. Nature 2021; 598: 597
17e Cai Y, Chatterjee S, Ritter T. J. Am. Chem. Soc. 2023; 145: 13542
17f Lu B, Zhang Z, Jiang M, Liang D, He Z.-W, Bao F.-S, Xiao W.-J, Chen J.-R. Angew. Chem. Int. Ed. 2023; 62: e202309460

18 Xia P.-J, Song D, Ye Z.-P, Hu Y.-Z, Xiao J.-A, Xiang H.-Y, Chen X.-Q, Yang H. Angew. Chem. Int. Ed. 2020; 59: 6706
19 Zhu C, Dong J, Liu X, Gao L, Zhao Y, Xie J, Li S, Zhu C. Angew. Chem. Int. Ed. 2020; 59: 12817
20 Miao Y.-Q, Li X.-Y, Pan Q.-J, Ma Y, Kang J.-X, Ma Y.-N, Liu Z, Chen X. Green Chem. 2022; 24: 7113
21 Wu X, Wang Y, Zhou M.-X, Chen Z, Peng X, Wang Z, Zeng Y.-F. Adv. Synth. Catal. 2023; 365: 3824
22 Xie F, Mao Z, Curran DP, Liang H, Dai W. Angew. Chem. Int. Ed. 2023; 62: e202306846
23 Miao Y.-Q, Pan Q.-J, Liu Z, Chen X. New J. Chem. 2022; 46: 19091
24 Zhu C, Yao S, Xie J. Synthesis 2024; 56: 1711
25 Li D.-C, Zeng J.-H, Yang Y.-H, Zhan Z.-P. Org. Chem. Front. 2023; 10: 2075
26 Chen Z.-L, Empel C, Wang K, Wu P.-P, Cai B.-G, Li L, Koenigs RM, Xuan J. Org. Lett. 2022; 24: 2232
27 Xie Y, Zhang R, Chen Z.-L, Rong M, He H, Ni S, He X.-K, Xiao W.-J, Xuan J. Adv. Sci. 2024; 11: 2306728
28 Zhou N, Yuan X.-A, Zhao Y, Xie J, Zhu C. Angew. Chem. Int. Ed. 2018; 57: 3990
29 Kawamoto T, Morioka T, Noguchi K, Curran DP, Kamimura A. Org. Lett. 2021; 23: 1825