Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds
- Corresponding author: Jia Qianfa, li_ychem@yznu.cn
Citation:
Li Yaqiong, Fan Yuhang, Jia Qianfa. Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds[J]. Chinese Journal of Organic Chemistry,
;2019, 39(2): 350-362.
doi:
10.6023/cjoc201806038
(a) Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242.
(b) Knappke, C. E. I.; Grupe, S.; Gä rtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828.
(c) Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793.
Wurtz, A. Ann. Chem. Pharm. 1855, 96, 364.
doi: 10.1002/(ISSN)1099-0690
Ullmann, F.; Bielecki, J. Chem. Ber. 1901, 34, 2174.
doi: 10.1002/(ISSN)1099-0682
(a) Hanna, L. E.; Jarvo, E. R. Angew. Chem., Int. Ed. 2015, 54, 15618.
(b) Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411.
(c) Weix, D. J. Acc. Chem. Res. 2015, 48, 1767.
Amatore, M.; Gosmini, C. Angew. Chem., Int. Ed. 2008, 47, 2089.
doi: 10.1002/(ISSN)1521-3773
(a) Takashi, K.; Hayashi, T. Tetrahedron Lett. 1997, 38, 7087.
(b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
(c) Schoenebeck, F.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 2496.
(d) Ackerman, L. K. G.; Lovell, M. M.; Weix, D. J. Nature 2015, 524, 454.
Olivares, A. M.; Weix, D. J. J. Am. Chem. Soc. 2018, 140, 2446.
(a) Fillon, H.; Gosmini, C.; Périchon, J. J. Am. Chem. Soc. 2003, 125, 3867.
(b) Sibille, S.; Ratovelomanana, V.; Périchon, J. J. Chem. Soc., Chem. Commun. 1992, 283.
(a) Denmark, S. E.; Butler, C. R. Chem. Commun. 2009, 20.
(b) Riviere, C.; Pawlus, A. D.; Merillon, J.-M. Nat. Prod. Rep. 2012, 29, 1317.
(c) Zhang, Z.; Qin, Y. Macromolecules 2016, 49, 3318.
(a) Moncomble, A.; Le Floch, P.; Lledos, A.; Gosmini, C. J. Org. Chem. 2012, 77, 5056.
(b) Amatore, M.; Gosmini, C.; Périchon, J. Eur. J. Org. Chem. 2005, 2005, 989.
(c) Gomes, P.; Gosmini, C.; Périchon, J. Tetrahedron 2003, 59, 2999.
Liu, J.; Ren, Q.; Zhang, X.; Gong, H. Angew. Chem., Int. Ed. 2016, 55, 15544.
doi: 10.1002/anie.201607959
(a) Ariafard, A.; Lin, Z. Organometallics 2006, 25, 4030.
(b) Cristian, M.; Maria, B.; Feliu, M.; Gregorio, A.; Mercedes, M. S. Chem.-Eur. J. 2010, 16, 13390.
(c) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674.
(a) Jones, G. D.; McFarland, C.; Anderson, T. J.; Vicic, D. A. Chem. Commun. 2005, 4211.
(b) González-Bobes, F.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 5360.
Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920.
doi: 10.1021/ja9093956
Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192.
doi: 10.1021/ja407589e
(a) Everson, D. A.; Jones, B. A.; Weix, D. J. J. Am. Chem. Soc. 2012, 134, 6146.
(b) Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 46, 5743.
(c) Takahashi, H.; Inagaki, S.; Nishihara, Y.; Shibata, T.; Takagi, K. Org. Lett. 2006, 8, 3037.
McCann, L. C.; Organ, M. G. Angew. Chem., Int. Ed. 2014, 53, 4386.
doi: 10.1002/anie.201400459
Everson, D. A.; Buonomo, J. A.; Weix, D. J. Synlett 2014, 25, 233.
Hansen, E. C.; Pedro, D. J.; Wotal, A. C.; Gower, N. J.; Nelson, J. D.; Caron, S.; Weix, D. J. Nat. Chem. 2016, 8, 1126.
doi: 10.1038/nchem.2587
Wang, X.; Wang, S.; Xue, W.; Gong, H. J. Am. Chem. Soc. 2015, 137, 11562.
doi: 10.1021/jacs.5b06255
(a) Rollin, Y.; Troupel, M.; Tuck, D. G.; Perichon, J. J. Organomet. Chem. 1986, 303, 131.
(b) Meyer, G.; Rollin, Y.; Perichon, J. J. Organomet. Chem. 1987, 333, 263.
(c) Gosmini, C.; Lasry, S.; Nedelec, J.-Y.; Perichon, J. Tetrahedron 1998, 54, 1289.
(d) Sengmany, S.; Vitu-Thiebaud, A.; Le Gall, E.; Condon, S.; Leonel, E.; Thobie-Gautier, C.; Pipelier, M.; Lebreton, J.; Dubreuil, D. J. Org. Chem. 2013, 78, 370.
(e) Perkins, R. J.; Pedro, D. J.; Hansen, E. C. Org. Lett. 2017, 19, 3755.
(a) Pratsch, G.; Overman, L. E. J. Org. Chem. 2015, 80, 11388.
(b) Duan, Z.; Li, W.; Lei, A. Org. Lett. 2016, 18, 4012.
(c) Zhang, P.; Le, C. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 8084.
(a) Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
(b) Zuo, Z.; Cong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 1832.
(a) Huihui, K. M. M.; Caputo, J. A.; Melchor, Z.; Olivares, A. M.; Spiewak, A. M.; Johnson, K. A.; DiBenedetto, T. A.; Kim, S.; Ackerman, L. K. G.; Weix, D. J. J. Am. Chem. Soc. 2016, 138, 5016.
(b) Zhang, X.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 13862.
(a) Liang, Z.; Xue, W.; . Lin, K.; Gong, H. Org. Lett. 2014, 16, 5620.
(b) Wang, J.; Zhao, J.; Gong, H. Chem. Commun. 2017, 53, 10180.
(c) Komeyama, K.; Ohata, R.; Kiguchi, S.; Osaka, I. Chem. Commun. 2017, 53, 6401.
Anka-Lufford, L. L.; Huihui, K. M. M.; Gower, N. J.; Ackerman, L. K. G.; Weix, D. J. Chem.-Eur. J. 2016, 22, 11564.
doi: 10.1002/chem.201602668
(a) Ackerman, L. K. G.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Chem. Sci. 2015, 6, 1115.
(b) Konev, M. O.; Hanna, L. E.; Jarvo, E. R. Angew. Chem., Int. Ed. 2016, 55, 6730.
(a) Anka-Lufford, L. L.; Prinsell, M. R.; Weix, D. J. J. Org. Chem. 2012, 77, 9989.
(b) Wang, S.; Qian, Q.; Gong, H. Org. Lett. 2012, 14, 3352.
(c) Gomes, P.; Gosmini, C.; Périchon, J. Org. Lett. 2003, 5, 1043.
Jia, X.-G.; Guo, P.; Duan, J.; Shu, X.-Z. Chem. Sci. 2018, 9, 640.
doi: 10.1039/C7SC03140H
Chen, F.; Chen, K.; Zhang, Y.; He, Y.; Wang, Y.-M.; Zhu, S. J. Am. Chem. Soc. 2017, 139, 13929.
doi: 10.1021/jacs.7b08064
(a) Cannes, C.; Condon, S.; Durandetti, M.; Périchon, J.; Nédélec, J.-Y. J. Org. Chem. 2000, 65, 4575.
(b) Qiu, C.; Yao, K.; Zhang, X.; Gong, H. Org. Biomol. Chem. 2016, 14, 11332.
(a) Johnson, K. A.; Biswas, S.; Weix, D. J. Chem.-Eur. J. 2016, 22, 7399.
(b) Gu, J.; Qiu, C.; Lu, W.; Qian, Q.; Lin, K.; Gong, H. Synthesis 2017, 49, 1867.
(c) Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 624.
(d) Patel, N. R.; Kelly, C. B.; Jouffroy, M.; Molander, G. A. Org. Lett. 2016, 18, 764.
Wotal, A. C.; Weix, D. J. Org. Lett. 2012, 14, 1476.
doi: 10.1021/ol300217x
Ni, S.; Zhang, W.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2017, 19, 2536.
doi: 10.1021/acs.orglett.7b00831
Yin, H.; Zhao, C.; You, H.; Lin, K.; Gong, H. Chem. Commun. 2012, 48, 7034.
doi: 10.1039/c2cc33232a
Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645.
doi: 10.1021/ja510653n
Wotal, A. C.; Ribson, R. D.; Weix, D. J. Organometallics 2014, 33, 5874.
doi: 10.1021/om5004682
Zheng, M.; Xue W.; Xue, T.; Gong, H. Org. Lett. 2016, 18, 6152.
doi: 10.1021/acs.orglett.6b03158
Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2015, 137, 10480.
doi: 10.1021/jacs.5b06466
Poremba, K. E.; Kadunce, N. T.; Suzuki, N.; Cherney, A. H.; Reisman, S. E. J. Am. Chem. Soc. 2017, 139, 5684.
doi: 10.1021/jacs.7b01705
(a) Evans, P. A.; Uraguchi, D. J. Am. Chem. Soc. 2003, 125, 7158.
(b) Alexakis, A.; El Hajjaji, S.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393.
(c) Cherney, A. H.; Reisman, S. E. J. Am. Chem. Soc. 2014, 136, 14365.
(d) Hofstra, J. L.; Cherney, A. H.; Ordner, C. M.; Reisman, S. E. J. Am. Chem. Soc. 2018, 140, 139.
Suzuki, N.; Hofstra, J. L.; Poremba, K. E.; Reisman, S. E. Org. Lett. 2017, 19, 2150.
doi: 10.1021/acs.orglett.7b00793
Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442.
doi: 10.1021/ja402922w
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