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1 article(s) from Dai, Mingji

Opportunities and challenges for direct C–H functionalization of piperazines

Zhishi Ye,
Kristen E. Gettys and
Mingji Dai

Beilstein J. Org. Chem. 2016, 12, 702–715, doi:10.3762/bjoc.12.70

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Graphical Abstract

Figure 1: Selected piperazine-containing small-molecule pharmaceuticals.

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Figure 2: Strategies for the synthesis of carbon-substituted piperazines.

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Figure 3: The first α-lithiation of N-Boc-protected piperazines by van Maarseveen et al. in 2005 [37].

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Figure 4: α-Lithiation of N-Boc-N’-tert-butyl piperazines by Coldham et al. in 2010 [38].

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Figure 5: Diamine-free α-lithiation of N-Boc-piperazines by O’Brien, Campos, et al. in 2010 [40].

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Figure 6: The first enantioselective α-lithiation of N-Boc-piperazines by McDermott et al. in 2008 [41].

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Figure 7: Dynamic thermodynamic resolution of lithiated of N-Boc-piperazines by Coldham et al. in 2010 [38].

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Figure 8: Enantioselective α-lithiation of N-Boc-N’-alkylpiperazines by O’Brien et al. in 2013 and 2016 [42,43].

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Figure 9: Asymmetric α-functionalization of N-Boc-piperazines with Ph₂CO by O’Brien et al. in 2016 [43].

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Figure 10: A “chiral auxiliary” strategy toward enantiopure α-functionalized piperazines by O’Brien et al. 201...

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Figure 11: Installation of methyl group at the α-position of piperazines by O’Brien et al. 2016 [43].

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Figure 12: α-Lithiation trapping of C-substituted N-Boc-piperazines by O’Brien et al. 2016 [43].

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Figure 13: Rh-catalyzed reactions of N-(2-pyridinyl)piperazines by Murai et al. in 1997 [52].

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Figure 14: Ta-catalyzed hydroaminoalkylation of piperazines by Schafer et al. in 2013 [55].

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Figure 15: Photoredox catalysis for α-C–H functionalization of piperazines by MacMillan et al. in 2011 and 201...

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Figure 16: Copper-catalyzed aerobic C–H oxidation of piperazines by Touré, Sames, et al. in 2013 [67].

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Figure 17: Free radical approach by Undheim et al. in 1994 [68].

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Figure 18: Anodic oxidation approach by Nyberg et al. in 1976 [70].

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Review

Published 13 Apr 2016

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