Subscribe to RSS
DOI: 10.1055/a-2085-4195
ortho-Heterobimetallic Arylene Complex: A New Platform for Regioselective Difunctionalization
The financial support from the National Natural Science Foundation of China (Grant No. 22171026, 21572022 and 21372031) is gratefully acknowledged.
![](https://www.thieme-connect.de/media/synlett/202317/lookinside/thumbnails/st-2023-p0149-sp_10-1055_a-2085-4195-1.jpg)
Abstract
Regioselective ortho difunctionalization of arenes is highly desirable yet challenging in organic synthesis. Here, we briefly discuss various methods for ortho difunctionalization of arenes and highlight a novel ortho-heterobimetallic arylene complex enabled by heterobimetallic synergism, which shows great potential in regioselective ortho difunctionalizations.
1 Introduction
2 Distinct Reactivity of C–Fe and C–Ti Bonds
3 E/E′ ODFs by Fe/Ti-Heterobimetallic Intermediate
4 Nu/E ODFs by Fe/Ti -Heterobimetallic Intermediate
5 Summary and Outlook
Publication History
Received: 09 April 2023
Accepted after revision: 03 May 2023
Accepted Manuscript online:
03 May 2023
Article published online:
26 May 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a García-López J.-A, Greaney MF. Chem. Soc. Rev. 2016; 45: 6766
- 1b Bhojgude SS, Bhunia A, Biju AT. Acc. Chem. Res. 2016; 49: 1658
- 1c Shi J, Li Y, Li Y. Chem. Soc. Rev. 2017; 46: 1707
- 1d Pozo I, Guitián E, Pérez D, Peña D. Acc. Chem. Res. 2019; 52: 2472
- 1e He J, Qiu D, Li Y. Acc. Chem. Res. 2020; 53: 508
- 1f Fluegel LL, Hoye TR. Chem. Rev. 2021; 121: 2413
- 1g Shi J, Li L, Li Y. Chem. Rev. 2021; 121: 3892
- 2 Medina JM, Mackey JL, Garg NK, Houk KN. J. Am. Chem. Soc. 2014; 136: 15798
- 3 Amano M, Saiga A, Ikegami R, Ogata T, Takagi K. Tetrahedron Lett. 1998; 39: 8667
- 4 Blümke TD, Klatt T, Koszinowski K, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 9926
- 5 Ilies L, Isomura M, Yamauchi S, Nakamura T, Nakamura E. J. Am. Chem. Soc. 2017; 139: 23
- 6 Catellani M, Frignani F, Rangoni A. Angew. Chem., Int. Ed. Engl. 1997; 36: 119
- 7 Della CaN, Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
- 8 Ye J, Lautens M. Nat. Chem. 2015; 7: 863
- 9 Wang J, Dong G. Chem. Rev. 2019; 119: 7478
- 10 Cheng H.-G, Jia S, Zhou Q. Acc. Chem. Res. 2023; 56: 573
- 11a Rahim A, Feng J, Gu Z. Chin. J. Chem. 2019; 37: 929
- 11b Li M.-Y, Wei D, Feng C.-G, Lin G.-Q. Chem. Asian J. 2022; 17: e202200456
- 12 Ge Y, Zhang J, Qiu Z, Xie Z. Angew. Chem. Int. Ed. 2020; 59: 4851
- 13 He Y, Börjesson M, Song H, Xue Y, Zeng D, Martin R, Zhu S. J. Am. Chem. Soc. 2021; 143: 20064
- 14a Liu KM, Liao LY, Duan XF. Chem. Commun. 2015; 51: 1124
- 14b Liu KM, Wei J, Duan XF. Chem. Commun. 2015; 51: 4655
- 14c Zhang R, Zhao Y, Liu KM, Duan XF. Org. Lett. 2018; 20: 7942
- 14d Wang L, Wei YM, Zhao Y, Duan XF. J. Org. Chem. 2019; 84: 5176
- 15a Wei YM, Ma XD. Wang M. F, Duan XF. J. Am. Chem. Soc. 2023; 145: 1542
- 15b Oestreich M, Klare HF. T, Bolomey EA. Synfacts 2023; 19: 0357
- 16 Okugawa Y, Hayashi Y, Kawauchi S, Hirano K, Miura M. Org. Lett. 2018; 20: 3670
- 17 Sanchez-Moreno M, Sanz AM, Gomez-Contreras F, Navarro P, Marin C, Ramirez-Macias I, Rosales MJ, Olmo F, Garcia-Aranda I, Campayo L, Cano C, Arrebola F, Yunta MJ. J. Med. Chem. 2011; 54: 970
- 18 Padhye S, Dandawate P, Yusufi M, Ahmad A, Sarkar FH. Med. Res. Rev. 2012; 32: 1131
- 19a Mohrle H, Folttmann H. Arch. Pharm. 1988; 321: 167
- 19b Bao N, Ou J, Shi W, Li N, Chen L, Sun J. Eur. J. Org. Chem. 2018; 2254
- 20 Luo H, Li Y, Du L, Xin X, Wang T, Han J, Tian Y, Li B. Org. Lett. 2021; 23: 7883
- 21a Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
- 21b Gu Q, Al Mamari HH, Graczyk K, Diers E, Ackermann L. Angew. Chem. Int. Ed. 2014; 53: 3868
- 21c Wei YM, Wang MF, Duan XF. Org. Lett. 2019; 21: 6471
- 22 Jopp S, Wallaschkowski T, Ehlers P, Frank E, Schneider G, Wölfling J, Mernyák E, Villinger A, Langer P. Tetrahedron 2018; 74: 2825