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Organic & Biomolecular Chemistry
DOI: 10.1039/C7OB02269G
COMMUNICATION
Organic & Biomolecular Chemistry
mechanistic investigations are underway and will be reported 11 N. A. Weires, E. L. Baker and N. K. Garg, Nat. Chem., 2016,
5.
2 X. Li and G. Zou, Chem. Commun., 2015, 51, 5089.
3 G. Meng, S. Shi and M. Szostak, ACS Catal., 2016,
8,
7
in due course.
Rutgers University and the NSF (CAREER CHE-1650766) are
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6, 7335.
acknowledged for support. The 500 MHz spectrometer was
supported by the NSF-MRI grant (CHE-1229030).
4 (a) C. Liu, G. Meng, Y. Liu, R. Liu, R. Lalancette, R. Szostak and
M. Szostak, Org. Lett., 2016, 18, 4194; (b) H. Wu, M. Cui, J.
Jian and Z. Zheng, Adv. Synth. Catal., 2016, 358, 3876; (c) For
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Notes and references
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2
Reviews: (a) R. Takise, K. Muto and J. Yamaguchi, Chem. Soc.
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General reviews on cross-coupling: (a) A. de Meijere, S. Bräse
and M. Oestreich, Metal-Catalyzed Cross-Coupling Reactions
and More, Wiley, 2014; (b) G. Molander, J. P. Wolfe and M.
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5 C. Liu, Y. Liu, R. Liu, R. Lalancette, R. Szostak and M. Szostak,
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8 S. Shi and M. Szostak, Synthesis, 2017, 49, 3602.
9 Reviews on acyl-metal intermediates: (a) L. J. Gooßen, N.
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,
ßen, Chem. Sci., 2012,
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intermediates, see: S. D. Friis, A. T. Lindhardt and T.
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2
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0 (a) For an example of using N-acylsuccinimides in SmI -
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,
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4
For representative acyl-couplings, see: (a) L. Hie, N. F. F.
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Houk and N. K. Garg, Nature, 2015, 524, 79; (b) P. Lei, G.
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For representative decarbonylative couplings, see: (a) G.
2
006, 4, 3553.
1 (a) For an elegant study on using N-acylsuccinimides as
acylating reagents, see: C. A. Goodman, J. B. Eagles, L.
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2 M. Cui, Z. Chen, T. Liu, H. Wang and Z. Zeng, Tetrahedron
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3 Note that the reference 22 incorrectly assigns the effect of
acid coordination to the amide bond in N-acylsuccinimides
2
Rueping, Angew. Chem. Int. Ed., 2017, 56, 3972.
5
For studies on the effect of amide bond geometry on cross-
coupling, see: (a) V. Pace, W. Holzer, G. Meng, S. Shi, R.
Lalancette, R. Szostak and M. Szostak, Chem. Eur. J., 2016,
and N-acylglutarimides. It has been
conclusiv5eal,yb
demonstrated that these amides favour O-protonation,
which is in contrast to bridged lactams, which favour N-
protonation: R. Szostak, J. Aubé and M. Szostak, Chem.
Commun., 2015, 51, 6395.
22, 14494; (b) R. Szostak, S. Shi, G. Meng, R. Lalancette and
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For the lead reference on electronic activation, see: (a) R.
Szostak, G. Meng and M. Szostak, M., J. Org. Chem., 2017,
82, 6373; (b) See also refs. 16 and 17.
For recent developments of new catalytic systems in amide
bond cross-coupling, see: Pd-NHC: (a) Ref. 3b; (b) P. Lei, G.
Meng, S. Shi, Y. Ling, J. An, R. Szostak and M. Szostak, Chem.
2
4 The following features additionally demonstrate the high
activity of the present catalytic system: (1) using the
22
alternative system, the yield drops significantly upon
lowering the Pd-loading to 3 mol%, which is a standard
protocol in the present method; (2) the present method
tolerates alkyl N-acylsuccinimide amides. Alkyl amides, in
general, are challenging substrates for cross-coupling. See
the following references that address this point: 7d and 7e.
Sci., 2017, 8, 6525; (c) P. Lei, G. Meng, Y. Ling, J. An and M.
Szostak, J. Org. Chem., 2017, 82, 6638; Ni-NHC: (d) L. Hie, E.
L. Baker, S. M. Anthony, J. N. Desrosiers, C. Senanayake and
N. K. Garg, Angew. Chem. Int. Ed., 2016, 55, 15129; (e) J. E.
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A. Greenberg, C. M. Breneman and J. F. Liebman, The Amide
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(a) G. Meng and M. Szostak, Org. Lett., 2015, 17, 4364; (b) G.
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0 For selected examples, see: (a) Ref. 4a-b, 4d-e, 9; (b) S. Shi
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