Radical-Mediated Difunctionalization of Styrenes

Xiazhen Bao; Jun Li; Wei Jiang; Congde Huo

doi:10.1055/s-0039-1690987

Synthesis, Table of Contents

Synthesis 2019; 51(24): 4507-4530
DOI: 10.1055/s-0039-1690987

review

Radical-Mediated Difunctionalization of Styrenes

Xiazhen Bao ‡

,

Jun Li ‡

,

Wei Jiang

,

Congde Huo∗

Abstract

All articles of this category

‡ These two authors contributed equally to this paper.

Abstract

Styrene, an extremely important compound in the chemical industry, is mainly produced by the dehydrogenation or oxidative dehydrogenation of ethylbenzene. Transformation of this raw organic material to more useful fine organic chemicals is a very significant topic. Recently, the radical difunctionalization of styrene has become a powerful and efficient tool for organic synthesis. This strategy can introduce two substituents into a styrene molecule in one step via addition to the C=C bond, enhancing the molecular complexity in a single operation with good selectivity and wide functional group compatibility.

1 Introduction

2 C-Centered Radicals

3 CF₃ and Other Polyfluoroalkyl Radicals

4 N-Centered Radicals

5 P-Centered Radicals

6 O-Centered Radicals

7 S-Centered Radicals

8 Other-Atom-Centered Radicals

9 Conclusion and Perspective

Key words

radical - difunctionalization - styrene - alkene - multicomponent reaction - step economy

Full Text

References

References
1 Bataille CJ. R, Donohoe TJ. Chem. Soc. Rev. 2011; 40: 114
2 Wu S, Zhou Y, Li Z. Chem. Commun. 2019; 55: 883
3 Gurram VR. B, Enumula SS, Koppadi KS, Chada RR, Burri DR, Kamaraju SR. R. Catal. Commun. 2019; 118: 1
4 Cavani F, Trifiro F. Appl. Catal., A 1995; 133: 219
5 Cheng K, Huang L, Zhang Y. Org. Lett. 2009; 11: 2908
6 Kim JY, Park JC, Song H, Park KH. Bull. Korean Chem. Soc. 2010; 31: 3509
7 Sun H, Zhang Y, Guo F, Zha Z, Wang Z. J. Org. Chem. 2012; 77: 3563
8 Yan Z, Wang N.-X, Gao X.-W, Li J.-L, Wu Y.-H, Zhang T, Chen S.-L, Xing Y. Adv. Synth. Catal. 2019; 361: 1007
9 Zhang W, Wang N.-X, Bai C.-B, Wang Y.-J, Lan X.-W, Xing Y, Li Y.-H, Wen J.-L. Sci. Rep. 2015; 5: 15250
10 Su R, Li Y, Min M.-Y, Ouyang X.-H, Song R.-J, Li J.-H. Chem. Commun. 2018; 54: 13511
11 Xie J, Huang Z.-Z. Chem. Commun. 2010; 46: 1947
12 Lan X.-W, Wang N.-X, Zhang W, Wen J.-L, Bai C.-B, Xing Y, Li Y.-H. Org. Lett. 2015; 17: 4460
13 Schweitzer-Chaput B, Demaerel J, Engler H, Klussmann M. Angew. Chem. Int. Ed. 2014; 53: 8737
14 Lan X.-W, Wang N.-X, Bai C.-B, Lan C.-L, Zhang T, Chen S.-L, Xing Y. Org. Lett. 2016; 18: 5986
15 Liu Y.-Y, Yang X.-H, Song R.-J, Luo S, Li J.-H. Nat. Commun. 2017; 8: 14720
16 Chatalova-Sazepin C, Wang Q, Sammis GM, Zhu J. Angew. Chem. Int. Ed. 2015; 54: 5443
17 Bunescu A, Ha TM, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2017; 56: 10555
18 Dong Y.-X, Li Y, Gu C.-C, Jiang S.-S, Song R.-J, Li J.-H. Org. Lett. 2018; 20: 7594
19 Li W.-Y, Wu C.-S, Wang Z, Yang L. Chem. Commun. 2018; 54: 11013
20 Liao Z, Yi H, Li Z, Fan C, Zhang X, Liu J, Deng Z, Lei A. Chem. Asian J. 2015; 10: 96
21 Pan G.-H, Song R.-J, Xie Y.-X, Luo S, Li J.-H. Synthesis 2018; 50: 1651
22 Yong X, Han Y.-F, Li Y, Song R.-J, Li J.-H. Chem. Commun. 2018; 54: 12816
23 Zhang Y.-X, Jin R.-X, Yin H, Li Y, Wang X.-S. Org. Lett. 2018; 20: 7283
24 Li W.-Y, Wang Q.-Q, Yang L. Org. Biomol. Chem. 2017; 15: 9987
25 Sha W, Deng L, Ni S, Mei H, Han J, Pan Y. ACS Catal. 2018; 8: 7489
26 Speckmeier E, Fuchs PJ. W, Zeitler K. Chem. Sci. 2018; 9: 7096
27 Liu W, Li Y, Liu K, Li Z. J. Am. Chem. Soc. 2011; 133: 10756
28 Yang W.-C, Weng S.-S, Ramasamy A, Rajeshwaren G, Liao Y.-Y, Chen C.-T. Org. Biomol. Chem. 2015; 13: 2385
29 Ge L, Li Y, Bao H. Org. Lett. 2019; 21: 256
30 Jiao Y, Chiou M.-F, Li Y, Bao H. ACS Catal. 2019; 9: 5191
31 Wang H, Guo L.-N, Duan X.-H. Chem. Commun. 2014; 50: 7382
32 Bu M, Niu TF, Cai C. Catal. Sci. Technol. 2015; 5: 830
33 Hoque IU, Chowdhury SR, Maity S. J. Org. Chem. 2019; 84: 3025
34 Yasu Y, Koike T, Akita M. Angew. Chem. Int. Ed. 2012; 51: 9567
35 Yasu Y, Koike T, Akita M. Org. Lett. 2013; 15: 2136
36 Dagousset G, Carboni A, Magnier E, Masson G. Org. Lett. 2014; 16: 4340
37 Wang F, Wang D, Wan X, Wu L, Chen P, Liu G. J. Am. Chem. Soc. 2016; 138: 15547
38 Li Y, Studer A. Angew. Chem. Int. Ed. 2012; 51: 8221
39 Egami H, Shimizu R, Sodeoka M. Tetrahedron Lett. 2012; 53: 5503
40 Ilchenko NO, Janson PG, Szabó KJ. J. Org. Chem. 2013; 78: 11087
41 Liang Z, Wang F, Chen P, Liu G. Org. Lett. 2015; 17: 2438
42 Wang F, Qi X, Liang Z, Chen P, Liu G. Angew. Chem. Int. Ed. 2014; 53: 1881
43 Yang M, Wang W, Liu Y, Feng L, Ju X. Chin. J. Chem. 2014; 32: 833
44 Tomita R, Yasu Y, Koike T, Akita M. Angew. Chem. Int. Ed. 2014; 53: 7144
45 Wu L, Wang F, Wan X, Wang D, Chen P, Liu G. J. Am. Chem. Soc. 2017; 139: 2904
46 Zhou S, Song T, Chen H, Liu Z, Shen H, Li C. Org. Lett. 2017; 19: 698
47 Deb A, Manna S, Modak A, Patra T, Maity S, Maiti D. Angew. Chem. Int. Ed. 2013; 52: 9747
48 Jiang X.-Y, Qing F.-L. Angew. Chem. Int. Ed. 2013; 52: 14177
49 Zhang H.-Y, Ge C, Zhao J, Zhang Y. Org. Lett. 2017; 19: 5260
50 Zhang L, Zhang G, Wang P, Li Y, Lei A. Org. Lett. 2018; 20: 7396
51 Wu Y.-B, Lu G.-P, Yuan T, Xu Z.-B, Wan L, Cai C. Chem. Commun. 2016; 52: 13668
52 Guo J.-Y, Wu R.-X, Jin J.-K, Tian S.-K. Org. Lett. 2016; 18: 3850
53 Valverde E, Kawamura S, Sekine D, Sodeoka M. Chem. Sci. 2018; 9: 7115
54 Yu J, Wu Z, Zhu C. Angew. Chem. Int. Ed. 2018; 57: 17156
55 Shi E, Liu J, Liu C, Shao Y, Wang H, Lv Y, Ji M, Bao X, Wan X. J. Org. Chem. 2016; 81: 5878
56 Li L, Huang M, Liu C, Xiao J.-C, Chen Q.-Y, Guo Y, Zhao Z.-G. Org. Lett. 2015; 17: 4714
57 Yi N, Zhang H, Xu C, Deng W, Wang R, Peng D, Zeng Z, Xiang J. Org. Lett. 2016; 18: 1780
58 Xu R, Cai C. Chem. Commun. 2019; 55: 4383
59 Xu L, Mou X.-Q, Chen Z.-M, Wang S.-H. Chem. Commun. 2014; 50: 10676
60 Sun X, Li X, Song S, Zhu Y, Liang Y.-F, Jiao N. J. Am. Chem. Soc. 2015; 137: 6059
61 Fu N, Sauer GS, Saha A, Loo A, Lin S. Science 2017; 357: 575
62 Hussain MI, Feng Y, Hu L, Deng Q, Zhang X, Xiong Y. J. Org. Chem. 2018; 83: 7852
63 Chen Y, Tian T, Li Z. Org. Chem. Front. 2019; 6: 632
64 Zhang H, Pu W, Xiong T, Li Y, Zhou X, Sun K, Liu Q, Zhang Q. Angew. Chem. Int. Ed. 2013; 52: 2529
65 Zhang H, Song Y, Zhao J, Zhang J, Zhang Q. Angew. Chem. Int. Ed. 2014; 53: 11079
66 Zhang B, Studer A. Org. Lett. 2014; 16: 1790
67 Li Y, Hartmann M, Daniliuc CG, Studer A. Chem. Commun. 2015; 51: 5706
68 Wan D, Wang F, Chen P, Lin Z, Liu G. Angew. Chem. Int. Ed. 2017; 56: 2054
69 Wang D, Wu L, Wang F, Wan X, Chen P, Lin Z, Liu G. J. Am. Chem. Soc. 2017; 139: 6811
70 Zhang B, Studer A. Org. Lett. 2013; 15: 4548
71 Fumagalli G, Rabet PT. G, Boyd S, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11481
72 Lu M.-Z, Wang C.-Q, Loh T.-P. Org. Lett. 2015; 17: 6110
73 Wang H, Zhang D, Bolm C. Chem. Eur. J. 2018; 24: 14942
74 Monos TM, McAtee RC, Stephenson CR. J. Science 2018; 361: 1369
75 Chumnanvej N, Samakkanad N, Pohmakotr M, Reutrakul V, Jaipetch T, Soorukram D, Kuhakarn C. RSC Adv. 2014; 4: 59726
76 Chen Y, Ma Y, Li L, Jiang H, Li Z. Org. Lett. 2019; 21: 1480
77 Wei W, Ji J.-X. Angew. Chem. Int. Ed. 2011; 50: 9097
78 Zhang G.-Y, Li C.-K, Li D.-P, Zeng R.-S, Shoberu A, Zou J.-P. Tetrahedron 2016; 72: 2972
79 Taniguchi T, Idota A, Yokoyama S, Ishibashi H. Tetrahedron Lett. 2011; 52: 4768
80 Gao Y, Wu J, Xu J, Zhang P, Tang G, Zhao Y. RSC Adv. 2014; 4: 51776
81 Zhou S.-F, Li D.-P, Liu K, Zou J.-P, Asekun OT. J. Org. Chem. 2015; 80: 1214
82 Zhang C, Li Z, Zhu L, Yu L, Wang Z, Li C. J. Am. Chem. Soc. 2013; 135: 14082
83 Xu J, Li X, Gao Y, Zhang L, Chen W, Fang H, Tang G, Zhao Y. Chem. Commun. 2015; 51: 11240
84 Li J.-A, Zhang P.-Z, Liu K, Shoberu A, Zou J.-P, Zhang W. Org. Lett. 2017; 19: 4704
85 Wang Y, Wang W, Tang R, Liu Z, Tao W, Fang Z. Org. Biomol. Chem. 2018; 16: 7782
86 Zhang P.-Z, Zhang L, Li J.-A, Shoberu A, Zou J.-P, Zhang W. Org. Lett. 2017; 19: 5537
87 Giglio BC, Schmidt VA, Alexanian EJ. J. Am. Chem. Soc. 2011; 133: 13320
88 Xia X.-F, Zhu S.-L, Gu Z, Wang H, Li W, Liu X, Liang Y.-M. J. Org. Chem. 2015; 80: 5572
89 Bag R, Sar D, Punniyamurthy T. Org. Lett. 2015; 17: 2010
90 Andia AA, Miner MR, Woerpel KA. Org. Lett. 2015; 17: 2704
91 Lu Q, Liu Z, Luo Y, Zhang G, Huang Z, Wang H, Liu C, Miller JT, Lei A. Org. Lett. 2015; 17: 3402
92 Xia X.-F, Gu Z, Liu W, Wang H, Xia Y, Gao H, Liu X, Liang Y.-M. J. Org. Chem. 2015; 80: 290
93 Liu C, Zhu M, Wei W, Yang D, Cui H, Liu X, Wang H. Org. Chem. Front. 2015; 2: 1356
94 Xue Q, Xie J, Xu P, Hu K, Cheng Y, Zhu C. ACS Catal. 2013; 3: 1365
95 Zhou S.-F, Pan X, Zhou Z.-H, Shoberu A, Zou J.-P. J. Org. Chem. 2015; 80: 3682
96 Huo C, Wang Y, Yuan Y, Chen F, Tang J. Chem. Commun. 2016; 52: 7233
97 Tehri P, Aegurula B, Peddinti RK. Tetrahedron Lett. 2017; 58: 2062
98 Wang Y, Deng L, Mei H, Du B, Han J, Pan Y. Green Chem. 2018; 20: 3444
99 Yu J, Gao C, Song Z, Yang H, Fu H. Org. Biomol. Chem. 2015; 13: 4846
100 Yuan Y, Chen Y, Tang S, Huang Z, Lei A. Sci. Adv. 2018; 4: eaat5312
101 Zheng Y, He Y, Rong G, Zhang X, Weng Y, Dong K, Xu X, Mao J. Org. Lett. 2015; 17: 5444
102 Cui H, Liu X, Wei W, Yang D, He C, Zhang T, Wang H. J. Org. Chem. 2016; 81: 2252
103 Wang D, Yan Z, Xie Q, Zhang R, Lin S, Wang Y. Org. Biomol. Chem. 2017; 15: 1998
104 Li X, Guo Y, Shen Z. J. Org. Chem. 2018; 83: 2818
105 Lu Q, Zhang J, Wei F, Qi Y, Wang H, Liu Z, Lei A. Angew. Chem. Int. Ed. 2013; 52: 7156
106 Wei W, Wen J, Yang D, Wu M, You J, Wang H. Org. Biomol. Chem. 2014; 12: 7678
107 Yang D, Huang B, Wei W, Li J, Lin G, Liu Y, Ding J, Sun P, Wang H. Green Chem. 2016; 18: 5630
108 Yuan Z, Wang H.-Y, Mu X, Chen P, Guo Y.-L, Liu G. J. Am. Chem. Soc. 2015; 137: 2468
109 Wei W, Liu X, Yang D, Dong R, Cui Y, Yuan F, Wang H. Tetrahedron Lett. 2015; 56: 1808
110 Kariya A, Yamaguchi T, Nobuta T, Tada N, Miura T, Itoh A. RSC Adv. 2014; 4: 13191
111 Taniguchi N. J. Org. Chem. 2015; 80: 7797
112 Chan C.-K, Lo N.-C, Chen P.-Y, Chang M.-Y. Synthesis 2017; 49: 4469
113 Singh AK, Chawla R, Yadav LD. S. Tetrahedron Lett. 2014; 55: 4742
114 Chawla R, Singh AK, Yadav LD. S. Eur. J. Org. Chem. 2014; 2032
115 Yang J, Liu Y.-Y, Song R.-J, Peng Z.-H, Li J.-H. Adv. Synth. Catal. 2016; 358: 2286
116 Wei W, Liu C, Yang D, Wen J, You J, Suo Y, Wang H. Chem. Commun. 2013; 49: 10239
117 Liu C, Ding L, Guo G, Liu W. Eur. J. Org. Chem. 2016; 910
118 Wan X, Sun K, Zhang G. Sci. China Chem. 2017; 60: 353
119 Yang F.-L, Wang F.-X, Wang T.-T, Wang Y.-J, Tian S.-K. Chem. Commun. 2014; 50: 2111
120 Yuan Y, Cao Y, Lin Y, Li Y, Huang Z, Lei A. ACS Catal. 2018; 8: 10871
121 Choudhuri K, Achar TK, Mal P. Adv. Synth. Catal. 2017; 359: 3566
122 Xu R, Li Z. Tetrahedron Lett. 2018; 59: 3942
123 Sun K, Lv Y, Zhu Z, Jiang Y, Qi J, Wu H, Zhang Z, Zhang G, Wang X. RSC Adv. 2015; 5: 50701
124 Singh AK, Chawla R, Keshari T, Yadav VK, Yadav LD. S. Org. Biomol. Chem. 2014; 12: 8550
125 Wang Y, Jiang W, Huo C. J. Org. Chem. 2017; 82: 10628
126 Zhang J, An Y, Wu J. Chem. Eur. J. 2017; 23: 9477
127 Shi X, Ren X, Ren Z, Li J, Wang Y, Yang S, Gu J, Gao Q, Huang G. Eur. J. Org. Chem. 2014; 5083
128 Gao X, Pan X, Gao J, Jiang H, Yuan G, Li Y. Org. Lett. 2015; 17: 1038
129 Wang H, Lu Q, Qian C, Liu C, Liu W, Chen K, Lei A. Angew. Chem. Int. Ed. 2016; 55: 1094
130 Yadav AK, Yadav LD. S. Green Chem. 2015; 17: 3515
131 Yadav AK, Yadav LD. S. Green Chem. 2016; 18: 4240
132 Yadav AK, Singh KN. Chem. Commun. 2018; 54: 1976
133 Fu N, Sauer GS, Lin S. J. Am. Chem. Soc. 2017; 139: 15548
134 Wang H, Chen C, Liu W, Zhu Z. Beilstein J. Org. Chem. 2017; 13: 2023
135 Sun L, Yuan Y, Yao M, Wang H, Wang D, Gao M, Chen Y.-H, Lei A. Org. Lett. 2019; 21: 1297
136 Dong H, Zhang L, Fang Z, Fu W, Tang T, Feng Y, Tang T. RSC Adv. 2017; 7: 22008
137 Yang Y, Song R.-J, Ouyang X.-H, Wang C.-Y, Li J.-H, Luo S. Angew. Chem. Int. Ed. 2017; 56: 7916
138 Saravanan P, Anbarasan P. Chem. Commun. 2019; 55: 4639