Chromium-Catalyzed Reductive Cleavage of Unactivated Aromatic and Benzylic C–O Bonds

Shuqing Yuan; Liang Ling; Jinghua Tang; Meiming Luo; Xiaoming Zeng

doi:10.1055/a-1507-6419

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(18): 3343-3350
DOI: 10.1055/a-1507-6419

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Chromium-Catalyzed Reductive Cleavage of Unactivated Aromatic and Benzylic C–O Bonds

Shuqing Yuan

,

Liang Ling

,

Jinghua Tang

,

Meiming Luo∗

,

Xiaoming Zeng ∗

Abstract

Alle Artikel dieser Rubrik

This work is dedicated to Professor Shinji Murai for his contribution to bond activation.

Abstract

Reductive cleavage of aromatic and benzylic C–O bonds by chromium catalysis is reported. This deoxygenative reaction was promoted by low-cost CrCl₂ precatalyst combined with poly(methyl hydrogen siloxane) as the mild reducing agent, providing a strategy in forming reduced motifs by cleavage of unactivated C–O bonds. A range of functional groups such as bromide, chloride, fluoride, hydroxyl, amino, and alkoxycarbonyl can be retained in the reduction.

Keywords

C–O bond - reduction - chromium - homogeneous catalysis

Volltext

Referenzen

References

1a Yu D.-G, Li B.-J, Shi Z.-J. Acc. Chem. Res. 2010; 43: 1486
1b Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
1c Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
1d Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
1e Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
1f Zeng H, Qiu Z, Domínguez-Huerta A, Hearne Z, Chen Z, Li C.-J. ACS Catal. 2017; 7: 510
1g Qiu Z, Li C.-J. Chem. Rev. 2020; 120: 10454
1h Li B.-J, Yu D.-G, Sun C.-L, Shi Z.-J. Chem. Eur. J. 2011; 17: 1728

2a Mori A, Mizusaki T, Ikawa T, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2007; 13: 1432
2b Sajiki H, Mori A, Mizusaki T, Ikawa T, Maegawa T, Hirota K. Org. Lett. 2006; 8: 987
2c Lipshutz BH, Frieman BA, Butler T, Kogan V. Angew. Chem. Int. Ed. 2006; 45: 800
2d Chow WK, So CM, Lau CP, Kwong FY. Org. Chem. Front. 2014; 1: 464

3a Jørgensen KB, Rantanen T, Dörfler T, Snieckus V. J. Org. Chem. 2015; 80: 9410
3b Mesganaw T, Fine Nathel NF, Garg NK. Org. Lett. 2012; 14: 2918
3c Yasui K, Higashino M, Chatani N, Tobisu M. Synlett 2017; 28: 2569
3d Kakiuchi F, Usui M, Ueno S, Chatani N, Murai S. J. Am. Chem. Soc. 2004; 126: 2706
3e Tobisu M, Shimasaki T, Chatani N. Angew. Chem. Int. Ed. 2008; 47: 4866
3f Guan B.-T, Wang Y, Li B.-J, Yu D.-G, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 14468
3g Schwarzer MC, Konno R, Hojo T, Ohtsuki A, Nakamura K, Yasutome A, Takahashi H, Shimasaki T, Tobisu M, Chatani N, Mori S. J. Am. Chem. Soc. 2017; 139: 10347
3h Zhao Y, Snieckus V. J. Am. Chem. Soc. 2014; 136: 11224

4 Xi X, Chen T, Zhanga J.-S, Han L.-B. Chem. Commun. 2018; 54: 1521

5a Li J, Wang Z.-X. Chem. Commun. 2018; 54: 2138
5b Wang Y, Shen J, Chen Q, Wang L, He M. Chin. Chem. Lett. 2019; 30: 409

6a Hibe Y, Ebe Y, Nishimura T, Yorimitsu H. Chem. Lett. 2017; 46: 953
6b Zhao Y, Snieckus V. Org. Lett. 2018; 20: 2826

7a Kusumoto S, Nozaki K. Nat. Commun. 2015; 6: 6296
7b Shi W.-J, Li X.-L, Lia Z.-W, Shi Z.-J. Org. Chem. Front. 2016; 3: 375
7c Ohgi A, Nakao Y. Chem. Lett. 2016; 45: 45

8a Ren Y, Yan M, Wang J, Zhang ZC, Yao K. Angew. Chem. Int. Ed. 2013; 52: 12674
8b Chatterjee M, Ishizaka T, Suzukia A, Kawanami H. Chem. Commun. 2013; 49: 4567

9 Álvarez-Bercedo P, Martin R. J. Am. Chem. Soc. 2010; 132: 17352
10 Cornella J, Gómez-Bengoa E, Martin R. J. Am. Chem. Soc. 2013; 135: 1997
11 Tobisu M, Yamakawa K, Shimasakia T, Chatani N. Chem. Commun. 2011; 47: 2946
12 Tobisu M, Morioka T, Ohtsukib A, Chatani N. Chem. Sci. 2015; 6: 3410
13 Igarashi T, Haito A, Chatani N, Tobisu M. ACS Catal. 2018; 8: 7475
14 Sergeev AG, Hartwig JF. Science 2011; 332: 439
15 Sergeev AG, Webb JD, Hartwig JF. J. Am. Chem. Soc. 2012; 134: 20226
16 See for a recent example of reductive cleavage of C(aryl)–O bonds by Rh-Al complex: Seki R, Hara N, Saito T, Nakao Y. J. Am. Chem. Soc. 2021; 143: 6388

Selected reviews of Cr catalysis:

17a Fürstner A. Chem. Rev. 1999; 99: 991
17b Agapie T. Coord. Chem. Rev. 2011; 255: 861
17c Li J, Knochel P. Synthesis 2019; 51: 2100
17d Zeng X, Cong X. Org. Chem. Front. 2015; 2: 69

Selected examples of Cr catalysis:

18a Murakami K, Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2007; 9: 1569
18b Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
18c Steib AK, Kuzmina OM, Fernandez S, Malhotra S, Knochel P. Chem. Eur. J. 2015; 21: 1961
18d Bellan AB, Kuzmina OM, Vetsova VA, Knochel P. Synthesis 2017; 49: 188
18e Yan J, Yoshikai N. Org. Lett. 2017; 19: 6630
18f Li J, Ren Q, Cheng X, Karaghiosoff K, Knochel P. J. Am. Chem. Soc. 2019; 141: 18127
18g Yin J, Li J, Wang G.-X, Yin Z.-B, Zhang W.-X, Xi Z. J. Am. Chem. Soc. 2019; 141: 4241

19a Cong X, Tang H, Zeng X. J. Am. Chem. Soc. 2015; 137: 14367
19b Cong X, Fan F, Ma P, Luo M, Chen H, Zeng X. J. Am. Chem. Soc. 2017; 139: 15182
19c Tang J, Luo M, Zeng X. Synlett 2017; 28: 2577
19d Tang J, Liu LL, Yang S, Cong X, Luo M, Zeng X. J. Am. Chem. Soc. 2020; 142: 7715
19e Tang J, Fan F, Cong X, Zhao L, Luo M, Zeng X. J. Am. Chem. Soc. 2020; 142: 12834

20 Somerville RJ, Hale LV. A, Gómez-Bengoa E, Burés J, Martin R. J. Am. Chem. Soc. 2018; 140: 8771

21a Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
21b Chen M, Doba T, Sato T, Razumkov H, Ilies L, Shang R, Nakamura E. J. Am. Chem. Soc. 2020; 142: 4883

22 Kim K, Lee J. Org. Lett. 2018; 20: 7712
23 Sharma R, Patel N, Vishwakarma R, Bharatam P, Bharate S. Chem. Commun. 2016; 52: 1009
24 Hibe Y, Ebe Y, Nishimura T, Yorimitsu H. Chem. Lett. 2017; 46: 953
25 Su B, Sasabe H, Pu Y, Nakayama K, Kido J. Adv. Mater. 2010; 22: 3311
26 Igarashi T, Haito A, Chatani N, Tobisu M. ACS Catal. 2018; 8: 7475
27 Saito K, Kondo K, Akiyama T. Org. Lett. 2015; 17: 3366
28 Luan X, Wu L, Drinkel E, Mariz R, Gatti M, Dorta R. Org. Lett. 2010; 12: 1912

Zusatzmaterial

Supporting Information