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Synthesis 2016; 48(17): 2781-2788
DOI: 10.1055/s-0035-15661438
DOI: 10.1055/s-0035-15661438
special topic
Selective C(8)–H Activation of Imidazopyridines Mediated by Cooperative Nickel–Aluminum Catalysis
Further Information
Publication History
Received: 23 February 2016
Accepted after revision: 17 March 2016
Publication Date:
15 June 2016 (online)
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This work is dedicated to the victims of the recent Tainan earthquake.
Abstract
A catalytic paradigm is described featuring a synergistic interaction between nickel, aluminum and different ligands to impart a rather remote C–H alkenylation of imidazo[1,5-a]pyridines at the C-8 position without the necessity of installing a directing group. The scope of the direct C–H activation reactions of various 5-aryl- and 3-arylimidazopyridines is established using different sterically hindered alkynes.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561438.
- Supporting Information
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References
- 1a Wang DH, Engle KM, Shi BF, Yu J.-Q. Science 2010; 327: 315
- 1b Chen X, Engle KM, Wang DH, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 1c Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
- 1d Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
- 1e Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 1f Chiusoli GP, Catellani M, Costa M, Motti E, Della Ca’ N, Maestri G. Coord. Chem. Rev. 2010; 254: 456
- 1g McGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447
- 1h Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
- 1i Godula K, Sames D. Science 2006; 312: 67
- 1j Albrecht M. Chem. Rev. 2010; 110: 576
- 1k Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
- 1l Satoh T, Miura M. Chem. Lett. 2007; 36: 200
- 1m Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
- 1n Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
- 1o Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
- 1p Ackermann L. Chem. Rev. 2011; 111: 1315
- 1q Ackermann L. Acc. Chem. Res. 2014; 47: 281
- 1r Li C.-J. Acc. Chem. Res. 2009; 42: 335
- 1s Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
- 1t Kim JH, Gensch T, Zhao D, Stegemann L, Strassert CA, Glorius F. Angew. Chem. Int. Ed. 2015; 54: 10975
- 2a Yamaguchi E, Shibahara F, Murai T. J. Org. Chem. 2011; 76: 6146
- 2b Shibahara F, Sugiura R, Yamaguchi E, Kitagawa A, Murai T. J. Org. Chem. 2009; 74: 3566
- 2c Shibahara F, Dohke Y, Murai T. J. Org. Chem. 2012; 77: 5381
- 2d Salassa L, Garino C, Albertino A, Volpi G, Nervi C, Gobetto R, Hardcastle KI. Organometallics 2008; 27: 1427
- 2e Volpi G, Garino C, Salassa L, Fiedler J, Hardcastle KI, Gobetto R, Nervi C. Chem. Eur. J. 2009; 15: 6415
- 3a Alcarazo M, Roseblade SJ, Cowley AR, Fernández R, Brown JM, Lassaletta JM. J. Am. Chem. Soc. 2005; 127: 3290
- 3b Burstein C, Lehmann CW, Glorius F. Tetrahedron 2005; 61: 6207
- 3c Hahn FE. Angew. Chem. Int. Ed. 2006; 45: 1348
- 3d Fürstner A, Alcarazo M, Krause H, Lehmann CW. J. Am. Chem. Soc. 2007; 129: 12676
- 3e Hutt JT, Aron ZD. Org. Lett. 2011; 13: 5256
- 4a Davey D, Erhardt PW, Lumma WC, Wiggins J, Sullivan M, Pang D, Cantor E. J. Med. Chem. 1987; 30: 1337
- 4b Ford NF, Browne LJ, Campbell T, Gemenden C, Goldstein R, Gude C, Wasley JW. F. J. Med. Chem. 1987; 30: 1337
- 4c Pettit GR, Collins JC, Knight JC, Herald DL, Nieman RA, Williams MD, Pettit RK. J. Nat. Prod. 2003; 66: 544
- 4d Calcul L, Longeon A, Mourabit AA, Guyot M, Bourguet-Kondracki M. Tetrahedron 2003; 59: 6539
- 4e Rajeshkumar V, Lee T.-H, Chuang S.-C. Org. Lett. 2013; 15: 1468
- 5a Shibahara F, Murai T. Asian J. Org. Chem. 2013; 2: 624
- 5b Liu B, Huang Y, Lan J, Song F, You J. Chem. Sci. 2013; 4: 2163
- 5c Yamaguchi E, Shibahara F, Murai T. Chem. Lett. 2011; 40: 939
- 5d Shibahara F, Dohke Y, Murai T. J. Org. Chem. 2012; 77: 5381
- 5e Huang C, Giokaris A, Gevorgyan V. Chem. Lett. 2011; 40: 1053
- 6a Tsai C.-C, Shih W.-C, Fang C.-H, Li C.-Y, Ong T.-G, Yap GP. A. J. Am. Chem. Soc. 2010; 132: 11887
- 6b Shih W.-C, Chen W.-C, Lai Y.-C, Yu M.-S, Ho J.-J, Yap GP. A, Ong T.-G. Org. Lett. 2012; 14: 2046
- 6c Lee W.-C, Wang C.-H, Lin Y.-H, Shih W.-C, Ong T.-G. Org. Lett. 2013; 15: 5358
- 7a Nakao Y, Idei H, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2009; 131: 15996
- 7b Nakao Y, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 2448
- 7c Nakao Y, Idei H, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2009; 131: 5070
- 7d Nakao Y, Morita E, Idei H, Hiyama T. J. Am. Chem. Soc. 2011; 133: 3264
- 7e Nakao Y, Yamada Y, Kashihara N, Hiyama T. J. Am. Chem. Soc. 2010; 132: 13666
- 8 Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 14952
- 9 Yu M.-S, Lee W.-C, Chen C.-H, Tsai F.-Y, Ong T.-G. Org. Lett. 2014; 16: 4826
- 10 See details in Table S3 in the Supporting Information.
- 11 Purification of Laboratory Chemicals . 6th ed.; Armarego WL. F, Christina CL. L. Butterworth-Heinemann; Burlington: 2009
- 12a Ardugngo AJ, Krafczyk R, Schmutzler R, Craig HA, Goerlich JR, Marshall WJ, Unverzagt M. Tetrahedron 1999; 55: 14523
- 12b Hintermann L. Beilstein J. Org. Chem. 2007; 3: 22
- 13 Tang P, Wang W, Ritter T. J. Am. Chem. Soc. 2011; 133: 11482
For selected reviews, see: