Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols

Feng-Feng Pan; Peng Guo; Xiaochuang Huang; Xing-Zhong Shu

doi:10.1055/a-1467-2432

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(17): 3094-3100
DOI: 10.1055/a-1467-2432

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols

Autor*innen

Feng-Feng Pan

^aState Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. of China

^bCollege of Chemical Engineering and Technology, Tianshui Normal University, 60 South Xihe Road, Tianshui, 741001, P. R. of China
Peng Guo

^aState Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. of China
Xiaochuang Huang

^cJiangsu Tasly Diyi Pharmaceutical Co., Ltd., 168 West Chaoyang Road, Huai’An, Jiangsu, 223003, P. R. of China
Xing-Zhong Shu ∗

^aState Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

Dibenzyls are essential building blocks that are widely used in organic synthesis, and they are typically prepared by the homocoupling of halides, organometallics, and ethers. Herein, we report an approach to this class of compounds using alcohols, which are more stable and readily available. The reaction proceeds via nickel-catalyzed and dimethyl oxalate assisted dynamic kinetic homocoupling of benzyl alcohols. Both primary and secondary alcohols are tolerated.

Key words

homocoupling - nickel - dibenzyls - alcohols - synthetic methodology

Volltext

Referenzen

References

1a Barrett TN, Braddock DC, Monta A, Webb MR, White AJ. P. J. Nat. Prod. 2011; 74: 1980
1b Zhu L.-J, Wang M.-Q, Qin Y, Wang M.-N, Zhang G.-Q, Niu L.-T, Chen J.-B, Zhang X, Yao X.-S. J. Asian Nat. Prod. Res. 2020; in press

2a Iwasa E, Hamashima Y, Fujishiro S, Hashizume D, Sodeoka M. Tetrahedron 2011; 67: 6587
2b Duan X.-J, Li X.-M, Wang B.-G. J. Nat. Prod. 2007; 70: 1210

3a Goldup SM, Leigh DA, McBurney RT, McGonigal PR, Plant A. Chem. Sci. 2010; 1: 383
3b Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 46: 5743
3c Mboyi CD, Gaillard S, Mabaye MD, Pannetier N, Renaud J.-L. Tetrahedron 2013; 69: 4875
3d Khan S, Ghatak A, Bhar S. Tetrahedron Lett. 2015; 56: 2480
3e Liu Y, Xiao S, Qi Y, Du F. Chem. Asian J. 2017; 12: 673

4 Cai Y, Qian X, Gosmini C. Adv. Synth. Catal. 2016; 358: 2427
5 Barrero AF, Herrador MM, Quílez del Moral JF, Arteaga P, Akssira M, El Hanbali F, Arteaga JF, Diéguez HR, Sánchez EM. J. Org. Chem. 2007; 72: 2251
6 Liu Y, Zhang D, Xiao S, Qi Y, Liu S. Asian J. Org. Chem. 2019; 8: 858
7 Xu X, Cheng D, Pei W. J. Org. Chem. 2006; 71: 6637
8 Sato K, Inoue Y, Mori T, Sakaue A, Tarui A, Omote M, Kumadaki I, Ando A. Org. Lett. 2014; 16: 3756

9a Lei A, Zhang X. Org. Lett. 2002; 4: 2285
9b Cahiez G, Moyeux A, Buendia J, Duplais C. J. Am. Chem. Soc. 2007; 129: 13788
9c Zhou Z, Xue W. J. Organomet. Chem. 2009; 694: 599
9d Zhu Y, Xiong T, Han W, Shi Y. Org. Lett. 2014; 16: 6144

10 Cao Z.-C, Shi Z.-J. J. Am. Chem. Soc. 2017; 139: 6546

11a Diederich F, Stang PJ. Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 1998
11b Kuwano R. Synthesis 2009; 7: 1049
11c Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
11d Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
11e Tollefson EJ, Hanna LE, Jarvo ER. Acc. Chem. Res. 2015; 48: 2344

12a A review: Pang X, Peng X, Shu X.-Z. Synthesis 2020; 52: 3751

Selected examples:

12b Qian X, Auffrant A, Felouat A, Gosmini C. Angew. Chem. Int. Ed. 2011; 50: 10402
12c Ackerman LK. G, Anka-Lufford LL, Naodovic M, Weix DJ. Chem. Sci. 2015; 6: 1115
12d Tollefson EJ, Erickson LW, Jarvo ER. J. Am. Chem. Soc. 2015; 137: 9760
12e Yan X.-B, Li C.-L, Jin W.-J, Guo P, Shu X.-Z. Chem. Sci. 2018; 9: 4529
12f Ye Y, Chen H, Sessler JL, Gong H. J. Am. Chem. Soc. 2019; 141: 820

Metal-catalyzed hydrogen-borrowing reactions:

13a Yang Q, Wang Q, Yu Z. Chem. Soc. Rev. 2015; 44: 2305
13b Corma A, Navas J, Sabater MJ. Chem. Rev. 2018; 118: 1410

Ru-catalyzed dehydroxylative reactions:

14a Lee D.-H, Kwon K.-H, Yi CS. Science 2011; 333: 1613
14b Lee D.-H, Kwon K.-H, Yi CS. J. Am. Chem. Soc. 2012; 134: 7325

Transition-metal-catalyzed functionalization of allylic alcohols:

15a Butta NA, Zhang W. Chem. Soc. Rev. 2015; 44: 7929
15b Yang B, Wang Z.-X. J. Org. Chem. 2017; 82: 4542
15c Jia X.-G, Guo P, Duan J.-C, Shu X.-Z. Chem. Sci. 2018; 9: 640

16 Metal-catalyzed coupling using strong basic nucleophiles: Yu D.-G, Wang X, Zhu R.-Y, Luo S, Zhang X.-B, Wang B.-Q, Wang L, Shi Z.-J. J. Am. Chem. Soc. 2012; 134: 14638

Ti-catalyzed radical dehydroxylative reaction:

17a Suga T, Ukaji Y. Org. Lett. 2018; 20: 7846
17b Xie H, Guo J, Wang Y.-Q, Wang K, Guo P, Su P.-F, Wang X, Shu X.-Z. J. Am. Chem. Soc. 2020; 142: 16787

18 Guo P, Wang K, Jin W.-J, Xie H, Qi L, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2021; 143: 513
19 It is possible that the oxalates undergo halide exchange to form benzyl halides, which can also react with nickel to form dimers. However, during the reactions, we have failed to detect any benzyl halides by GC-MS.

20a Biswas S, Weix DJ. J. Am. Chem. Soc. 2013; 135: 16192
20b Weix DJ. Acc. Chem. Res. 2015; 48: 1767
20c Diccianni JB, Diao T. Trends Chem. 2019; 1: 830

21a He R.-D, Li C.-L, Pan Q.-Q, Guo P, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2019; 141: 12481
21b Ref 17b

22 Wang P.-Z, Chen J.-R, Xiao W.-J. Org. Biomol. Chem. 2019; 17: 6936
23 Nwachukwu CI, McFadden TP, Roberts AG. J. Org. Chem. 2020; 85: 9979
24 Park G, Yi SY, Jung J.-H, Cho EJ, You Y.-M. Chem. Eur. J. 2016; 22: 17790
25 Hu Y.-L, Li F, Gu G.-L, Lu M. Catal. Lett. 2011; 141: 467
26 Manley DW, Walton JC. Org. Lett. 2014; 16: 5394
27 Li Y.-J, Izumi T. Synth. Commun. 2003; 33: 3583
28 Wakui H, Kawasaki S, Satoh T, Miura M, Nomura M. J. Am. Chem. Soc. 2004; 126: 8658

Zusatzmaterial

Supporting Information (PDF) (opens in new window)