Communication
ChemComm
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D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey, J. L.
Leaser, Jr., R. J. Linderman, K. Lorenz, J. Manley, B. A. Pearlman,
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(
c) J. Bariwal and E. Van der Eycken, Chem. Soc. Rev., 2013, 42, 9283.
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8
For a review on Chan–Lam amination, see: J. X. Qiao and
P. Y. S. Lam, Synthesis, 2011, 829.
For a recent advance in Chan–Lam coupling, see: J. C. Vantourout,
H. N. Miras, A. Isidro-Llobet, S. Sproules and A. J. B. Watson, J. Am.
Chem. Soc., 2017, 139, 4769.
9
For an elegant approach to umpolung amination, see: T. J. Baker
and E. R. Jarvo, J. Am. Chem. Soc., 2009, 131, 15598 and references
cited therein.
1
2
Fig. 2 Kinetic profile of 1a (PhCO
2
Ph-NH
2
(2.0 equiv.), [4a] (3 mol%), K
CO
(3.0 equiv.), DME, 110 1C.
134, 13573; (c) K. Muto, J. Yamaguchi, D. G. Musaev and K. Itami,
Nat. Commun., 2015, 6, 7508.
2 Review: (a) C. Liu and M. Szostak, Chem. – Eur. J., 2017, 23, 7157; Select
examples: (b) G. Meng and M. Szostak, Org. Lett., 2015, 17, 4364;
supporting common catalytic manifold of esters and amides for
catalytic acyl C–X amination. Efforts toward expanding the
scope and synthesis of improved Pd–NHC catalysts are currently
ongoing and will be reported in due course. Further evaluation
1
(
c) G. Meng, S. Shi and M. Szostak, ACS Catal., 2016, 6, 7335;
(d) G. Meng and M. Szostak, Angew. Chem., Int. Ed., 2015, 54, 14518;
(
e) S. Shi, G. Meng and M. Szostak, Angew. Chem., Int. Ed., 2016, 55, 6959.
of well-defined Pd–NHC precatalysts will lay a foundation for 13 Reviews on C–O activation: (a) J. Cornella, C. Zarate and R. Martin,
Chem. Soc. Rev., 2014, 43, 8081; (b) M. Tobisu and N. Chatani, Acc.
Chem. Res., 2015, 48, 1717; (c) E. J. Tollefson, L. E. Hanna and
general applications of acyl Buchwald–Hartwig cross-coupling
in the synthesis of amides.
E. R. Jarvo, Acc. Chem. Res., 2015, 48, 2344.
Rutgers University and the NSF (CAREER CHE-1650766) are 14 R. Szostak, G. Meng and M. Szostak, J. Org. Chem., 2017, 82, 6373
and references cited therein.
5 Amides: (a) P. Lei, G. Meng and M. Szostak, ACS Catal., 2017,
acknowledged for support. The 500 MHz spectrometer was
supported by the NSF-MRI grant (CHE-1229030).
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, 1960; (b) G. Meng, P. Lei and M. Szostak, Org. Lett., 2017,
9, 2158; (c) P. Lei, G. Meng, Y. Ling, J. An and M. Szostak, J. Org.
Chem., 2017, 82, 6638; Esters: (d) T. B. Halima, W. Zhang, I. Yalaoui,
X. Hong, Y. F. Yang, K. N. Houk and S. G. Newman, J. Am. Chem.
Soc., 2017, 139, 1311; (e) T. B. Halima, J. K. Vandavasi, M. Shkoor
and S. G. Newman, ACS Catal., 2017, 7, 2176; ( f ) P. Lei, G. Meng,
S. Shi, Y. Ling, J. An, R. Szostak and M. Szostak, Chem. Sci., 2017, 8, 6525.
Pertinent Ni-catalyzed decarbonylative amination: (g) H. Yue, L. Guo,
H. H. Liao, Y. Cai, C. Zhu and M. Rueping, Angew. Chem., Int. Ed., 2017,
56, 4282. Pertinent Ni-catalyzed amination: (h) J. E. Dander and
N. K. Garg, ACS Catal., 2017, 2, 1413; (i) For previous studies using
Pd- and Ni-NHC catalysts, see: ref. 15b, e and h.
Conflicts of interest
There are no conflicts to declare.
Notes and references
1
A. Greenberg, C. M. Breneman and J. F. Liebman, The Amide Linkage:
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Reviews: (a) R. Marcia de Figueiredo, J. S. Suppo and J. M. Campagne,
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Peptides: (a) V. R. Pattabiraman and J. W. Bode, Nature, 2011,
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80, 471; Pharmaceuticals: (b) S. D. Roughley and A. M. Jordan, 18 (a) E. A. B. Kantchev, C. J. O’Brien and M. G. Organ, Angew. Chem.,
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chemistry: (e) D. G. Brown and J. Bostr ¨o m, J. Med. Chem., 2016,
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Selected recent reports on amide bonds: (a) Y. Chen, A. Turlik and
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C. Jamieson, I. Simpson and A. J. B. Watson, Chem. Commun., 2015,
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1, 9495; (c) R. Y. Zhu, M. E. Farmer, Y. Q. Chen and J. Q. Yu, Angew.
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G. Pelletier and A. B. Charette, Nat. Chem., 2012, 4, 228; ( f ) S. Das,
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Chem. Commun.
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