Recent advances in synthesis of organosilicons via radical strategies
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* Corresponding author.
E-mail address: glu@njust.edu.cn(G. Lu).
Citation: Xueping Zhang, Jingkun Fang, Chun Cai, Guoping Lu. Recent advances in synthesis of organosilicons via radical strategies[J]. Chinese Chemical Letters, ;2021, 32(4): 1280-1292. doi: 10.1016/j.cclet.2020.09.058
M.A. Brook, Silicon in Organic, Organometallic and Polymer Chemistry, John Wiley & Sons Ltd., Chichester, 2000.
K.L. Lee, Angew. Chem. Int. Ed. 56(2017) 3665-3669.
doi: 10.1002/anie.201612460
A.K. Franz, S.O. Wilson, J. Med. Chem. 56(2013) 388-405.
doi: 10.1021/jm3010114
A.G. Schafer, J.M. Wieting, A.E. Mattson, Org. Lett. 13(2011) 5228-5231.
doi: 10.1021/ol2021115
A.M. Hardman-Baldwin, A.E. Mattson, ChemSusChem 7(2014) 3275-3278.
doi: 10.1002/cssc.201402783
J.M. Wieting, T.J. Fisher, A.G. Schafer, M.D. Visco, Eur. J. Org. Chem. 3(2015) 525-533.
J. Hu, A.X. Zhang, L. Chen, W.Q. Li, X.H. Zeng, Silicone Mater. 33(2019) 218-246.
S.E. Denmark, C.S. Regens, Acc. Chem. Res. 41(2008) 1486-1499.
doi: 10.1021/ar800037p
C. Chatgilialoglu, Acc. Chem. Res. 25(1992) 188-194.
doi: 10.1021/ar00016a003
A.E. Portera, N. Patela, J.N. Skepperb, S.M. Besta, W. Bonfielda, Biomaterials 25(2004) 3303-3314.
doi: 10.1016/j.biomaterials.2003.10.006
R. Jugdaohsingh, K.L. Tucker, N. Qiao, et al., J. Bone Miner. Res. 19(2004) 296-307.
W.X. Xu, H.L. Teng, Y. Luo, et al., Chem. Asian J. 15(2020) 753-756.
doi: 10.1002/asia.202000089
T. Komiyama, Y. Minami, T. Hiyama, ACS Catal. 7(2017) 631-651.
doi: 10.1021/acscatal.6b02374
J. Scharfbier, M. Oestreich, Synlett 27(2016) 1274-1276.
doi: 10.1055/s-0035-1561407
J. Jia, X.Q. Zeng, Z.L. Liu, et al., Org. Lett. 22(2020) 2816-2821.
doi: 10.1021/acs.orglett.0c00809
B. Raya, S. Jing, V. Balasanthiran, T.V. RajanBabu, ACS Catal. 7(2017) 2275-2283.
doi: 10.1021/acscatal.6b03373
L. Omann, M. Oestreich, Organometallics 36(2017) 767-776.
doi: 10.1021/acs.organomet.6b00801
Z.Y. Cheng, S.P. Xing, J. Guo, et al., Chin. J. Chem. 37(2019) 457-461.
doi: 10.1002/cjoc.201900079
H.B. Peng, J.T. Yu, Y. Jiang, J. Cheng, Org. Biomol. Chem. 13(2015) 10299-10302.
doi: 10.1039/C5OB01855B
H. Qrareya, D. Dondi, D. Ravelli, M. Fagnoni, ChemCatChem 7(2015) 3350-3357.
doi: 10.1002/cctc.201500562
Z. Cao, Q. Zhua, Y.W. Lin, W.M. He, Chin. Chem. Lett. 30(2019) 2132-2138.
doi: 10.1016/j.cclet.2019.09.041
K.J. Liu, T.Y. Zeng, J.L. Zeng, et al., Chin. Chem. Lett. 30(2019) 2304-2308.
doi: 10.1016/j.cclet.2019.10.031
X.J. Shang, Z.Q. Liu, Org. Biomol. Chem. 14(2016) 7829-7831.
doi: 10.1039/C6OB00797J
J.S. Li, J. Wu, ChemPhotoChem 2(2018) 839-846.
doi: 10.1002/cptc.201800110
H.T. Huang, T. Li, J.Z. Wang, G.P. Qin, T.B. Xiao, Chin. J. Org. Chem. 39(2019) 1511-1521.
doi: 10.6023/cjoc201903078
J.R. Wilkinson, C.E. Nuyen, T.S. Carpenter, S.R. Harruff, R.V. Hoveln, ACS Catal. 9(2019) 8961-8979.
doi: 10.1021/acscatal.9b02762
L. Xu, S. Zhang, P.F. Li, Org. Chem. Front. 2(2015) 459-463.
doi: 10.1039/C5QO00012B
Y.M. Lin, G.P. Lu, R.K. Wang, W.B. Yi, Org. Lett. 19(2017) 1100-1103.
doi: 10.1021/acs.orglett.7b00126
R. Sakamoto, B.N. Nguyen, K. Maruoka, Asian J. Org. Chem. 7(2018) 1085-1088.
doi: 10.1002/ajoc.201800282
C. Zhang, J.X. Pi, L. Wang, P. Liu, P.P. Sun, Org. Biomol. Chem. 16(2018) 9223-9229.
doi: 10.1039/C8OB02670J
X.H. Chang, Z.L. Wang, M. Zhao, et al., Org. Lett. 22(2020) 1326-1330.
doi: 10.1021/acs.orglett.9b04645
L.Z. Zhang, D. Liu, Z.Q. Liu, Org. Lett. 17(2015) 2534-2537.
doi: 10.1021/acs.orglett.5b01067
J. Gu, C. Cai, Chem. Commun. 52(2016) 10779-10782.
doi: 10.1039/C6CC05509E
L.Z. Zhang, Z.J. Hang, Z.Q. Liu, Angew. Chem. Int. Ed. 55(2016) 236-239.
doi: 10.1002/anie.201509537
Y. Lan, X.H. Chang, P. Fan, et al., ACS Catal. 7(2017) 7120-7125.
doi: 10.1021/acscatal.7b02754
Z.F. Yan, J. Xie, C.J. Zhu, Adv. Synth. Catal. 359(2017) 4153-4157.
doi: 10.1002/adsc.201700926
Y. Yang, R.J. Song, X.H. Ouyang, et al., Angew. Chem. Int. Ed. 56(2017) 7916-7919.
doi: 10.1002/anie.201702349
Z.B. Xu, L. Chai, Z.Q. Liu, Org. Lett. 19(2017) 5573-5576.
doi: 10.1021/acs.orglett.7b02717
H. Zhang, X.X. Wu, Q. Zhao, C. Zhu, Chem. Asian J. 13(2018) 2453-2457.
doi: 10.1002/asia.201800150
R. Xu, C. Cai, Catal. Commun. 107(2018) 5-8.
doi: 10.1016/j.catcom.2017.12.023
S.H. Liu, P. Pan, H.Q. Fan, et al., Chem. Sci. 10(2019) 3817-3825.
doi: 10.1039/C9SC00046A
X. Zhang, M.X. Liu, T.L. Wang, et al., Org. Chem. Front. 6(2019) 3365-3368.
doi: 10.1039/C9QO00819E
D. Leifert, A. Studer, Org. Lett. 17(2015) 386-389.
doi: 10.1021/ol503574k
A. Studer, D.P. Curran, Nat. Chem. 6(2014) 765-773.
doi: 10.1038/nchem.2031
C. Yang, J. Wang, J.H. Li, et al., Adv. Synth. Catal. 360(2018) 3049-3054.
doi: 10.1002/adsc.201800417
J.P. Barham, G. Coulthard, T. McGuire, T. Tuttle, J.A. Murphy, J. Am. Chem. Soc. 138(2016) 7402-7410.
doi: 10.1021/jacs.6b03282
M. Rueping, M. Leiendecker, A. Das, T. Poisson, L. Bui, Chem. Commun. 47(2011) 10629-10631.
doi: 10.1039/c1cc14297f
E. Shirakawa, T. Hayashi, Chem. Lett. 41(2012) 130-134.
doi: 10.1246/cl.2012.130
E. Doni, S.Z. Zhou, J.A. Murphy, Molecules 20(2015) 1755-1774.
doi: 10.3390/molecules20021755
A.A. Toutov, W.B. Liu, K.N. Betz, et al., Nature 518(2015) 80-84.
doi: 10.1038/nature14126
A. Fedorov, A.A. Toutov, N.A. Swisher, R.H. Grubbs, Chem. Sci. 4(2013) 1640-1645.
doi: 10.1039/c3sc22256j
A.A. Toutov, W.B. Liu, K.N. Betz, B.M. Stoltz, R.H. Grubbs, Nat. Protoc. 10(2015) 1897-1903.
doi: 10.1038/nprot.2015.118
S. Banerjee, Y.F. Yang, I.D. Jenkins, et al., J. Am. Chem. Soc. 139(2017) 6880-6887.
doi: 10.1021/jacs.6b13032
W.B. Liu, D.P. Schuman, Y.F. Yang, et al., J. Am. Chem. Soc. 139(2017) 6867-6879.
doi: 10.1021/jacs.6b13031
N.A. Romero, D.A. Nicewicz, Chem. Rev. 116(2016) 10075-10166.
doi: 10.1021/acs.chemrev.6b00057
R. Brimioulle, D. Lenhart, M.M. Maturi, T. Bach, Angew. Chem. Int. Ed. 54(2015) 3872-3890.
doi: 10.1002/anie.201411409
K.L. Skubi, T.R. Blum, T.P. Yoon, Chem. Rev. 116(2016) 10035-10074.
doi: 10.1021/acs.chemrev.6b00018
J. Xuan, W.J. Xiao, Angew. Chem. Int. Ed. 51(2012) 6828-6838.
doi: 10.1002/anie.201200223
L.Y. Xie, T.G. Fang, J.X. Tan, et al., Green Chem. 21(2019) 3858-3863.
doi: 10.1039/C9GC01175G
L.L. Wang, M. Zhang, Y.L. Zhang, et al., Chin. Chem. Lett. 31(2020) 67-70.
doi: 10.1016/j.cclet.2019.05.041
R. Zhou, Y.Y. Goh, H.W. Liu, et al., Angew. Chem. Int. Ed. 56(2017) 16621-16625.
doi: 10.1002/anie.201711250
J. Hou, A. Ee, H. Cao, H.W. Ong, J.H. Xu, J. Wu, Angew. Chem. Int. Ed. 57(2018) 17220-17224.
doi: 10.1002/anie.201811266
D. Wei, R. Buhaibeh, Y. Canac, J.B. Sortais, Org. Lett. 21(2019) 7713-7716.
doi: 10.1021/acs.orglett.9b02449
N.X. Xu, B.X. Li, C. Wang, M. Uchiyama, Angew. Chem. Int. Ed. 59(2020) 2-8.
doi: 10.1002/anie.201914768
Z.K. Zhang, X.L. Hu, ACS Catal. 10(2020) 777-782.
doi: 10.1021/acscatal.9b04916
W.C. Xue, Z.W. Qu, S. Grimme, M. Oestreich, J. Am. Chem. Soc. 138(2016) 14222-14225.
doi: 10.1021/jacs.6b09596
W.C. Xue, M. Oestreich, Angew. Chem. Int. Ed. 56(2017) 11649-11652.
doi: 10.1002/anie.201706611
H. Hazrati, M. Oestreich, Org. Lett. 20(2018) 5367-5369.
doi: 10.1021/acs.orglett.8b02281
L.J. Cheng, N.P. Mankad, J. Am. Chem. Soc. 142(2020) 80-84.
doi: 10.1021/jacs.9b12043
S. Kramer, F. Hejjo, K.H. Rasmussen, S. Kegnæs, ACS Catal. 8(2018) 754-759.
doi: 10.1021/acscatal.7b02788
J.P. Oswald, K.A. Woerpel, J. Org. Chem. 84(2019) 7564-7574.
doi: 10.1021/acs.joc.9b00642
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Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
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