Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides

Qingchen Zhang; Xuan Wang; Qun Qian; Hegui Gong

doi:10.1055/s-0035-1562442

Synthesis, Table of Contents

Synthesis 2016; 48(17): 2829-2836
DOI: 10.1055/s-0035-1562442

special topic

Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides

Authors

Qingchen Zhang

^aCenter for Supramolecular Materials and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
Xuan Wang

^aCenter for Supramolecular Materials and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
Qun Qian*

^aCenter for Supramolecular Materials and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
Hegui Gong*

^aCenter for Supramolecular Materials and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

^bShanghai Key Lab of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China Email: hegui_gong@shu.edu.cn Email: Qianqun@shu.edu.cn

Abstract

All articles of this category

Abstract

Systematic studies of the coupling of benzylic with aryl halides are presented. The optimized reaction conditions for electron-deficient aryl halides cannot be applied to the electron-rich or neutral counterparts, and vice versa. The excellent functional group tolerance and broad substrate scope may enable the current work to be useful for the construction of diaryl methane products.

Key words

nickel - cross-coupling - arylation - alkyl halide - catalysis

Full Text

References

References

For reviews, see:

1a Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
1b Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793
1c Knappke CE. I, Grupe S, Gartner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem. Eur. J. 2014; 20: 6828
1d Weix DJ. Acc. Chem. Res. 2015; 48: 1767
1e Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
1f Nédélec JY, Perichon J, Troupel M. Top. Curr. Chem. 1997; 185: 141

For catalytic C(sp³)−C(sp³) bond formation through cross-coupling of alkyl electrophiles, see:

2a Yu X, Yang T, Wang S, Xu H, Gong H. Org. Lett. 2011; 13: 2138
2b Xu H, Zhao C, Qian Q, Deng W, Gong H. Chem. Sci. 2013; 4: 4022
2c Liang Z, Xue W, Lin K, Gong H. Org. Lett. 2014; 16: 4684
2d Xue W, Xu H, Liang Z, Qian Q, Gong H. Org. Lett. 2014; 16: 4984

For selected examples of allylation of alkyl halides, see:

3a Dai Y, Wu F, Zang Z, You H, Gong H. Chem. Eur. J. 2012; 18: 808
3b Anka-Lufford LL, Prinsell MR, Weix DJ. J. Org. Chem. 2012; 77: 9989
3c Qian X, Auffrant A, Felouat A, Gosmini C. Angew. Chem. Int. Ed. 2011; 50: 10402

For dimerization of two alkyl electrophiles, see:

4a Peng Y, Luo L, Yan C.-S, Zhang J.-J, Wang Y.-W. J. Org. Chem. 2013; 78: 10960
4b Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 5743
4c Goldup SM, Leigh DA, McBurney RT, McGonigal PR, Plant A. Chem. Sci. 2010; 1: 383

For selected examples for alkyl–aryl bond formation, see:

5a Everson DA, Shrestha R, Weix DJ. J. Am. Chem. Soc. 2010; 132: 920
5b Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
5c Yan C.-S, Peng Y, Xu X.-B, Wang Y.-W. Chem. Eur. J. 2012; 18: 6039
5d Molander GA, Traister KM, O’Neill BT. J. Org. Chem. 2015; 80: 2907
5e Wang S, Qian Q, Gong H. Org. Lett. 2012; 14: 3352

For selected examples for alkyl-acyl bond formation, see:

6a Wu F, Lu W, Qian Q, Ren Q, Gong H. Org. Lett. 2012; 14: 3044
6b Yin H, Zhao C, You H, Lin Q, Gong H. Chem. Commun. 2012; 48: 7034
6c Zhao C, Jia X, Wang X, Gong H. J. Am. Chem. Soc. 2014; 136: 17645
6d Wotal AC, Weix DJ. Org. Lett. 2012; 14: 1476
6e Jia X, Zhang X, Qian Q, Gong H. Chem. Commun. 2015; 51: 10302

For coupling involving generation of organometallic reagents in situ, see:

7a Krasovskiy A, Duplais C, Lipshutz BH. J. Am. Chem. Soc. 2009; 131: 15592
7b Czaplik WM, Mayer M, von Wangelin AJ. Angew. Chem. Int. Ed. 2009; 48: 607
7c Liu J.-H, Yang C.-T, Lu X.-Y, Zhang Z.-Q, Xu L, Cui M, Lu X, Xiao B, Fu Y, Liu L. Chem. Eur. J. 2014; 20: 15334

8a Cherney AH, Reisman SE. J. Am. Chem. Soc. 2014; 136: 14365
8b Cherney AH, Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2013; 135: 7442
8c Kadunce NT, Reisman SE. J. Am. Chem. Soc. 2015; 137: 10480

9a Moragas T, Gaydou M, Martin R. Angew. Chem. Int. Ed. 2016; 55: 5053
9b Leon T, Correa A, Martin R. J. Am. Chem. Soc. 2013; 135: 1221

10a Acker LK. G, Anka-Lufford LL, Naodovic M, Weix DJ. Chem. Sci. 2015; 6: 1115
10b Durandetti M, Gosmini C, Perichon J. Tetrahedron 2007; 63: 1146

11a Tellis JC, Primer DN, Monlander GA. Science 2014; 345: 433
11b Ryu D, Primer DN, Tellis JC, Molander GA. Chem. Eur. J. 2016; 22: 120
11c Gutierrez O, Tellis JC, Primer DN, Monlander GA, Kozlowski MC. J. Am. Chem. Soc. 2015; 137: 4896

12 Arendt KM, Doyle AG. Angew. Chem. Int. Ed. 2015; 54: 9876
13 Iwai Y, Gligorich KM, Sigman MS. Angew. Chem. Int. Ed. 2008; 47: 3219
14 Liu Z, Dong N, Xu M, Sun Z, Tu T. J. Org. Chem. 2013; 78: 7436
15 Saini V, Liao L, Wang Q, Jana R, Sigman M. Org. Lett. 2013; 15: 5008
16 Wang X, Guram A, Caille S, Hu J, Preston J, Ronk M, Walker S. Org. Lett. 2011; 13: 1881
17 Schäfer G, Bode J. Angew. Chem. Int. Ed. 2011; 50: 10913
18 Bedford RB, Brenner PB, Carter E, Clifton J, Cogswell PM, Gower NJ, Haddow MF, Harvey JN, Kehl JA, Murphy DM, Neeve EC, Neidig ML, Nunn J, Snyder BE. R, Taylor J. Organometallics 2014; 33: 5767
19 Mo X, Yakiwchuk J, Dansereau J, McCubbin A, Hall D. J. Am. Chem. Soc. 2015; 137: 9694
20 Pernia G, Kilburn J, Essex J, Mortishire-Smith R, Rowley M. J. Am. Chem. Soc. 1996; 118: 10220
21 Maity P, Shacklady-MeAtee D, Yap G, Sirianni E, Watson M. J. Am. Chem. Soc. 2013; 135: 280

Supplementary Material

Supporting Information (PDF)