Chromium-Catalyzed Cross-Coupling Reactions by Selective Activation of Chemically Inert Aromatic C–O, C–N, and C–H Bonds

Xuefeng Cong; Xiaoming Zeng

doi:10.1055/a-1507-4153

Synlett, Table of Contents

Synlett 2021; 32(13): 1343-1353
DOI: 10.1055/a-1507-4153

cluster account

Perspectives on Organoheteroatom and Organometallic Chemistry

Chromium-Catalyzed Cross-Coupling Reactions by Selective Activation of Chemically Inert Aromatic C–O, C–N, and C–H Bonds

Xuefeng Cong

,

Xiaoming Zeng ∗

Abstract

All articles of this category

Abstract

Transition-metal-catalyzed cross-coupling has emerged as one of the most powerful and useful tools for the formation of C–C and C–heteroatom bonds. Given the shortage of resources of precious metals on Earth, the use of Earth-abundant metals as catalysts in developing cost-effective strategies for cross-coupling is a current trend in synthetic chemistry. Compared with the achievements made using first-row nickel, iron, cobalt, and even manganese catalysts, the group 6 metal chromium has rarely been used to promote cross-coupling. This perspective covers recent advances in chromium-catalyzed cross-coupling reactions in transformations of chemically inert C(aryl)–O, C(aryl)–N, and C(aryl)–H bonds, offering selective strategies for molecule construction. The ability of low-valent Cr with a high-spin state to participate in two-electron oxidative addition is highlighted; this is different from the mechanism involving single-electron transfer that is usually assigned to chromium-mediated transformations.

1 Introduction

2 Chromium-Catalyzed Kumada Coupling of Nonactivated C(aryl)–O and C(aryl)–N Bonds

3 Chromium-Catalyzed Reductive Cross-Coupling of Two Nonactivated C(aryl)–Heteroatom Bonds

4 Chromium-Catalyzed Functionalization of Nonactivated C(aryl)–H Bonds

5 Conclusions and Outlook

Key words

chromium catalysis - homogeneous catalysis - cross-coupling

Full Text

References

References and Notes
1 Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Vol. 1. de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
2 Science of Synthesis: Cross Coupling and Heck-Type Reactions 1: C–C Cross Coupling Using Organometallic Partners. Molander GA. Thieme; Stuttgart: 2013
3 Science of Synthesis: Cross Coupling and Heck-Type Reactions 2: C–C Cross Coupling of Acidic C–H Nucleophiles, Wolfe J. P. Thieme; Stuttgart: 2013
4 Science of Synthesis: Cross Coupling and Heck-Type Reactions 3: C–C Cross Coupling Via C–H Activation. Larhed M. Thieme; Stuttgart 2013:
5 Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
6 Negishi E.-i. Angew. Chem. Int. Ed. 2011; 50: 6738
7 Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Developments, Molnár A. Wiley–VCH; Weinheim: 2013

8a Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
8b Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
8c Wang J, Dong G. Chem. Rev. 2019; 119: 7478

9a Fagnou K, Lautens M. Chem. Rev. 2003; 103: 169
9b Hayashi T, Yamasaki K. Chem. Rev. 2003; 103: 2829
9c Song G, Li X. Acc. Chem. Res. 2015; 48: 1007

For selected reviews, see:

10a Trost BM, Toste FD, Pinkerton AB. Chem. Rev. 2001; 101: 2067
10b Gunanathan C, Milstein D. Chem. Rev. 2014; 114: 12024

11a Ni- and Fe-Based Cross-Coupling Reactions . Correa A. Springer International; Cham: 2017
11b Standley EA, Tasker SZ, Jensen KL, Jamison TF. Acc. Chem. Res. 2015; 48: 1503
11c Diccianni J, Lin Q, Diao T. Acc. Chem. Res. 2020; 53: 906

12a Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
12b Sun C.-L, Li B.-J, Shi Z.-J. Chem. Rev. 2011; 111: 1293
12c Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
12d Nakamura M, Matsuo K, Ito S, Nakamura E. J. Am. Chem. Soc. 2004; 126: 3686
12e Shang R, Ilies L, Matsumoto A, Nakamura E. J. Am. Chem. Soc. 2013; 135: 6030
12f Shang R, Ilies L, Asako S, Nakamura E. J. Am. Chem. Soc. 2014; 136: 14349
12g Shang R, Ilies L, Nakamura E. J. Am. Chem. Soc. 2015; 137: 7660
12h Shang R, Ilies L, Nakamura E. J. Am. Chem. Soc. 2016; 138: 10132
12i Ilies L, Itabashi Y, Shang R, Nakamura E. ACS Catal. 2017; 7: 89
12j Doba T, Matsubara T, Ilies L, Shang R, Nakamura E. Nat. Catal. 2019; 2: 400
12k Nakamura E, Yoshikai N. J. Org. Chem. 2010; 75: 6061
12l Nakamura E, Sato K. Nat. Mater. 2011; 10: 158

13a Gao K, Yoshikai N. Acc. Chem. Res. 2014; 47: 1208
13b Cheng J, Wang L, Wang P, Deng L. Chem. Rev. 2018; 118: 9930
13c Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435
13d Liu W, Sahoo B, Junge K, Beller M. Acc. Chem. Res. 2018; 51: 1858

14a Hu Y, Zhou B, Wang C. Acc. Chem. Res. 2018; 51: 816
14b Liu W, Groves JT. Acc. Chem. Res. 2015; 48: 1727

15a Fürstner A. Chem. Rev. 1999; 99: 991
15b Agapie T. Coord. Chem. Rev. 2011; 255: 861
15c Zeng X, Cong X. Org. Chem. Front. 2015; 2: 69
15d Li J, Knochel P. Synthesis 2019; 51: 2100

16a Kochi JK, Singleton DM. J. Am. Chem. Soc. 1968; 90: 1582
16b Okude Y, Hirano S, Hiyama T, Nozaki H. J. Am. Chem. Soc. 1977; 99: 3179
16c Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
16d Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H. J. Am. Chem. Soc. 1986; 108: 6048

17 Gil A, Albericio F, Álvarez M. Chem. Rev. 2017; 117: 8420

18a Fürstner A, Shi N. J. Am. Chem. Soc. 1996; 118: 2533
18b Fürstner A, Shi N. J. Am. Chem. Soc. 1996; 118: 12349

19a Schwarz JL, Schäfers F, Tlahuext-Aca A, Lückemeier L, Glorius F. J. Am. Chem. Soc. 2018; 140: 12705
19b Schwarz JL, Huang H.-M, Paulisch TO, Glorius F. ACS Catal. 2020; 10: 1621
19c Xiong Y, Zhang G. Org. Lett. 2016; 18: 5094
19d Hirao Y, Katayama Y, Mitsunuma H, Kanai M. Org. Lett. 2020; 22: 8584
19e Schwarz JL, Kleinmans R, Paulisch TO, Glorius F. J. Am. Chem. Soc. 2020; 142: 2168
19f Kang JY, Connell BT. J. Am. Chem. Soc. 2010; 132: 7826
19g Usanov DL, Yamamoto H. J. Am. Chem. Soc. 2011; 133: 1286
19h Liu X, Li X, Chen Y, Hu Y, Kishi Y. J. Am. Chem. Soc. 2012; 134: 6136
19i Smith KM. Coord. Chem. Rev 2006; 250: 1023

20a Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
20b Yu D.-G, Li B.-J, Shi Z.-J. Acc. Chem. Res. 2010; 43: 1486
20c Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
20d Pang X, He R.-D, Shu X.-Z. Synlett 2020; 31: 635

21 Wenkert E, Michelotti EL, Swindell CS. J. Am. Chem. Soc. 1979; 101: 2246
22 Dankwardt JW. Angew. Chem. Int. Ed. 2004; 43: 2428

23a Tobisu M, Shimasaki T, Chatani N. Angew. Chem. Int. Ed. 2008; 47: 4866
23b Kakiuchi F, Usui M, Ueno S, Chatani N, Murai S. J. Am. Chem. Soc. 2004; 126: 2706
23c Ueno S, Mizushima E, Chatani N, Kakiuchi F. J. Am. Chem. Soc. 2006; 128: 16516
23d Guan B.-T, Xiang S.-K, Wang B.-Q, Sun Z.-P, Wang Y, Zhao K.-Q, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 3268
23e Álvarez-Bercedo P, Martin R. J. Am. Chem. Soc. 2010; 132: 17352
23f Zhao Y, Snieckus V. J. Am. Chem. Soc. 2014; 136: 11224

24a Murakami K, Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2007; 9: 1569
24b Yan J, Yoshikai N. Org. Lett. 2017; 19: 6630
24c Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
24d Yan J, Yoshikai N. Org. Chem. Front. 2017; 4: 1972
24e Hirscher NA, Sierra DP, Agapie T. J. Am. Chem. Soc. 2019; 141: 6022
24f Yin J, Li J, Wang G.-X, Yin Z.-B, Zhang W.-X, Xi Z. J. Am. Chem. Soc. 2019; 141: 4241

25 Cong X, Tang H, Zeng X. J. Am. Chem. Soc. 2015; 137: 14367
26 Tang J, Luo M, Zeng X. Synlett 2017; 28: 2577
27 Rong Z, Luo M, Zeng X. Org. Lett. 2019; 21: 6869

28a Li J, Ren Q, Cheng X, Karaghiosoff K, Knochel P. J. Am. Chem. Soc. 2019; 141: 18127
28b Steib AK, Kuzmina OM, Fernandez S, Malhotra S, Knochel P. Chem. Eur. J. 2015; 21: 1961
28c Bellan AB, Kuzmina OM, Vetsova VA, Knochel P. Synthesis 2017; 49: 188

29 Fan F, Tang J, Luo M, Zeng X. J. Org. Chem. 2018; 83: 13549

30a Ouyang K, Hao W, Zhang W.-X, Xi Z. Chem. Rev. 2015; 115: 12045
30b Wang Q, Su Y, Li L, Huang H. Chem. Soc. Rev. 2016; 45: 1257
30c García-Cárceles J, Bahou KA, Bower JF. ACS Catal. 2020; 10: 12738

31a Ueno S, Chatani N, Kakiuchi F. J. Am. Chem. Soc. 2007; 129: 6098
31b Koreeda T, Kochi T, Kakiuchi F. J. Am. Chem. Soc. 2009; 131: 7238
31c Tobisu M, Nakamura K, Chatani N. J. Am. Chem. Soc. 2014; 136: 5587

32 Blanksby SJ, Ellison GB. Acc. Chem. Res. 2003; 36: 255
33 Cong X, Fan F, Ma P, Luo M, Chen H, Zeng X. J. Am. Chem. Soc. 2017; 139: 15182

34a Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793
34b Weix DJ. Acc. Chem. Res. 2015; 48: 1767
34c Liu J, Ye Y, Sessler JL, Gong H. Acc. Chem. Res. 2020; 53: 1833

35a Ackerman LK. G, Lovell MM, Weix DJ. Nature 2015; 524: 454
35b Huang L, Ackerman LK. G, Kang K, Parsons A, Weix DJ. J. Am. Chem. Soc. 2019; 141: 10978

36 Cao Z.-C, Shi Z.-J. J. Am. Chem. Soc. 2017; 139: 6546
37 Tang J, Liu LL, Yang S, Cong X, Luo M, Zeng X. J. Am. Chem. Soc. 2020; 142: 7715
38 Tang J, Fan F, Cong X, Zhao L, Luo M, Zeng X. J. Am. Chem. Soc. 2020; 142: 12834

39a Zhao Q, Meng G, Nolan SP, Szostak M. Chem. Rev. 2020; 120: 1981
39b He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
39c Rej S, Ano Y, Chatani N. Chem. Rev. 2020; 120: 1788
39d Yi H, Zhang G, Wang H, Huang Z, Wang J, Singh AK, Lei A. Chem. Rev. 2017; 117: 9016
39e Li C.-J. Wuli Huaxue Xuebao 2019; 35: 905
39f Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
39g Dong Z, Ren Z, Thompson SJ, Xu Y, Dong G. Chem. Rev. 2017; 117: 9333
39h Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787

40 Kuzmina OM, Knochel P. Org. Lett. 2014; 16: 5208
41 Tang J, Liu P, Zeng X. Chem. Commun. 2018; 54: 9325
42 Chen M, Doba T, Sato T, Razumkov H, Ilies L, Shang R, Nakamura E. J. Am. Chem. Soc. 2020; 142: 4883
43 Li Y, Deng G, Zeng X. Organometallics 2016; 35: 747
44 Liu P, Chen C, Cong X, Tang J, Zeng X. Nat. Commun. 2018; 9: 4637