Dearomatization–Rearomatization Strategy for Palladium-Catalyzed C–N Cross-Coupling Reactions

Yatao Lang; Chao-Jun Li; Huiying Zeng

doi:10.1055/s-0040-1705901

Synlett, Table of Contents

Synlett 2021; 32(05): 429-435
DOI: 10.1055/s-0040-1705901

cluster

The Power of Transition Metals: An Unending Well-Spring of New Reactivity

Dearomatization–Rearomatization Strategy for Palladium-Catalyzed C–N Cross-Coupling Reactions

Yatao Lang

^aThe State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou, 730000, P. R. of China Email: zenghy@lzu.edu.cn

,

Chao-Jun Li∗

^bDepartment of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada Email: cj.li@mcgill.ca

,

Huiying Zeng ∗

^aThe State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou, 730000, P. R. of China Email: zenghy@lzu.edu.cn

› Author Affiliations

Abstract

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Dedicated to Professor Barry. M. Trost on the occasion of his 80^th birthday

Abstract

Substituted aromatic compounds play important roles in materials, biological agents, dyes, etc. Thus, the synthesis of substituted aromatic compounds has been a hot topic throughout the history of organic chemistry. Traditionally, the Friedel–Crafts reaction was a powerful tool for synthesizing substituted aromatic compounds. In recent decades, metal-catalyzed cross-coupling reactions were well developed via carbon–heteroatom bond cleavage, however, having difficulties towards some strong bonds, such as C(Ar)–OH. To overcome such challenges, newer strategies are needed. In this review, we summarize the recent efforts in the development of dearomatization–rearomatization strategy for cross-coupling reactions via C(Ar)–O bond cleavage.

1 Introduction

2 Dearomatization–Rearomatization Strategy for Cross-Coupling of Phenols

3 Dearomatization–Rearomatization Strategy for Cross-Coupling of Biphenols

4 Dearomatization–Rearomatization Strategy for Cross-Coupling of Diphenyl Ethers

5 Dearomatization–Rearomatization Strategy for Cross-Coupling of Indoles

6 Summary

Key words

dearomatization–rearomatization strategy - C(Ar)–O bond cleavage - cross-coupling reaction - transition-metal catalyzed - aromatic compounds

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References

References
1 Janovec L, Janockova J, Matejova M, Konkolova E, Paulikova H, Lichancova D, Junosova L, Hamulakova S, Imrich J, Kozurkova M. Bioorg. Chem. 2019; 83: 487
2 Cui J, Zhang S. Color. Technol. 2018; 134: 381
3 Niu H, Kang H, Cai J, Wang C, Bai X, Wang W. Polym. Chem. 2011; 2: 2804
4 Sanjeeva Rao K, Wu T.-S. Tetrahedron 2012; 68: 7735
5 Zakzeski J, Bruijnincx PC, Jongerius AL, Weckhuysen BM. Chem. Rev. 2010; 110: 3552
6 Zeng H, Qiu Z, Dominguez-Huerta A, Hearne Z, Chen Z, Li C.-J. ACS Catal. 2017; 7: 510
7 Barker RS. US3272865, 1966
8 Ono Y, Ishida H. J. Catal. 1981; 72: 121
9 Chen Z, Zeng H, Girard SA, Wang F, Chen N, Li C.-J. Angew. Chem. Int. Ed. 2015; 54: 14487
10 Chen Z, Zeng H, Gong H, Wang H, Li C.-J. Chem. Sci. 2015; 6: 4174
11 Tomkins P, Valgaeren C, Adriaensen K, Cuypers T, De Vos DE.. J. Catal. 2019; 371: 207
12 Li J.-S, Qiu Z, Li C.-J. Adv. Synth. Catal. 2017; 359: 3648
13 Cuypers T, Tomkins P, De Vos DE. Catal. Sci. Technol. 2018; 8: 2519
14 Qiu Z, Lv L, Li J, Li C.-C, Li C.-J. Chem. Sci. 2019; 10: 4775
15 Dominguez-Huerta A, Perepichka I, Li C.-J. ChemSusChem 2019; 12: 2999
16 Chen X, Yang Z, Chen X, Liang W, Zhu Z, Xie F, Li Y. J. Org. Chem. 2019; 85: 508
17 St Amant AH, Frazier CP, Newmeyer B, Fruehauf KR, Read de Alaniz J. Org. Biomol. Chem. 2016; 14: 5520
18 Cao D, Yu J, Zeng H, Li C.-J. J. Agric. Food Chem. 2020; in press;
19 Sanderson K. Nature 2011; 474: S12
20 Huber GW, Iborra S, Corma A. Chem. Rev. 2006; 106: 4044
21 Zeng H, Cao D, Qiu Z, Li C.-J. Angew. Chem. Int. Ed. 2018; 57: 3752
22 Wang M, Gutierrez OY, Camaioni DM, Lercher JA. Angew. Chem. Int. Ed. 2018; 57: 3747
23 Cao D, Zeng H, Li C.-J. ACS Catal. 2018; 8: 8873
24 Dou Q, Li C.-J, Zeng H. Chem. Sci. 2020; 11: 5740
25 Wang Z, Zeng H, Li C.-J. Org. Lett. 2019; 21: 2302