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Organic & Biomolecular Chemistry
Page 14 of 15
ARTICLE
Journal Name
Sudalai, Tetrahedron Lett., 2007, 48, 65; (e) Y. Sohtome, N.
Takemura, K. Takada, R. Takagi, T. Iguchi and K. Nagasawa,
Chem. Asian J., 2007,
Chouthaiwale, G. Suryavanshi, V. B. Chavan and A. Sudalai,
Chem. Commun., 2010, 46, 5012 ; (g) I. L. Miranda, I. K. B.
Lopes, M. A. N. Diaz and G. Diaz, Molecules, 2016, 21, 1176.
(a) D. J. Diekema and R. N. Jones, Drugs, 2000, 59, 7; (b) S.
DOI: 10.1039/C7OB00378A
2
, 1150; (f) R. S. Reddy, P. V. 11 Selected examples: (a) C. Kim and S. Y. Ko, Bull. Korean
Chem. Soc., 2011, 32, 4450; (b) J. A. Birrell and E. N.
Jacobsen, Org. Lett., 2013, 15, 2895; (c) C. Beattie and M.
North, RSC Adv., 2014,
4
, 31345; (d) J. Shang, Z. Li, C. Su, Y.
, 71765.
3
Guo and Y. Deng, RSC Adv., 2015,
5
Hanessian and K. K. Kothakonda, Can. J. Chem., 2005, 83, 80; 12 Selected examples: (a) A. Buzas and F. Gagosz, Synlett, 2006,
(c) A. R. Renslo, G. W. Luehr and M. F. Gordeev, Bioorg. Med.
Chem., 2006, 14, 4227; (d) K. Michalska, I. Karpiuk, M. Król
and S. Tyski, Bioorg. Med. Chem., 2013, 21, 577; (e) M.
Nasibullah, F. Hassan, N. Ahmad, A. R. Khan and M. Rahman,
2727; (b) K. J. Fraunhoffer and M. C. White, J. Am. Chem.
Soc., 2007, 129, 7274; (c) E.-S. Lee, H.-S. Yeom, J.-H. Hwang
and S. Shin, Eur. J. Org. Chem., 2007, 3503; (d) J. Ye, S. Li and
S. Ma, Org. Lett., 2012, 14, 2312; (e) H.-S. Yoon, J.-H. Kim, E.
J. Kang and H.-Y. Jang, Eur. J. Org. Chem., 2012, 2012, 1901;
(f) J. Zhao and H. Jiang, Tetrahedron Lett., 2012, 53, 6999;
(g) S. K. Alamsetti, A. K. A. Persson and J.-E. Baeckvall, Org.
Lett., 2014, 16, 1440; (h) T. J. Osberger and M. C. White, J.
Am. Chem. Soc., 2014, 136, 11176; (i) J. Hu, J. Ma, Q. Zhu, Z.
Adv. Sci., Eng. Med., 2015, 7, 91; (f) O. A. Phillips, R. D'Silva,
T. O. Bahta, L. H. Sharaf, E. E. Udo, L. Benov and D. Eric
Walters, Eur. J. Med. Chem., 2015, 106, 120.
4
5
(a) B. B. Lohray, S. Baskaran, B. S. Rao, B. Y. Reddy and I. N.
Rao, Tetrahedron Lett., 1999, 40, 4855; (b) J. R. Gage, W. R.
Perrault, T.-J. Poel and R. C. Thomas, Tetrahedron Lett.,
2000, 41, 4301; (c) M. R. Barbachyn and C. W. Ford, Angew.
Chem. Int. Ed., 2003, 42, 2010.
Zhang, C. Wu and B. Han, Angew. Chem., Int. Ed., 2015, 54
,
5399.
13 Review: P. Thansandote and M. Lautens, Chem. Eur. J., 2009,
15, 5874.
Selected examples: (a) D. A. Evans, J. M. Takacs, L. R. McGee,
M. D. Ennis, D. J. Mathre and J. Bartroli, Pure Appl. Chem., 14 (a) C. G. Espino and J. Du Bois, Angew. Chem. Int. Ed., 2001,
1981, 53, 1109; (b) D. A. Evans, Aldrichimica Acta, 1982, 15
,
40, 598; (b) A. Padwa, A. C. Flick, C. A. Leverett and T.
Stengel, J. Org. Chem., 2004, 69, 6377; (c) R. D. Grigg, J. W.
23; (c) S. Chavda, E. Coulbeck, M. Dingjan, J. Eames, A. Flinn
and J. Northen, Tetrahedron: Asymmetry, 2008, 19, 1536; (d)
D. J. Kerr, M. Miletic, J. H. Chaplin, J. M. White and B. L.
Flynn, Org. Lett., 2012, 14, 1732;
Rigoli, S. D. Pearce and J. M. Schomaker, Org. Lett., 2012, 14
280.
,
15 (a) Y. Cui and C. He, Angew. Chem. Int. Ed., 2004, 43, 4210;
(b) J. W. Rigoli, C. D. Weatherly, J. M. Alderson, B. T. Vo and
J. M. Schomaker, J. Am. Chem. Soc., 2013, 135, 17238.
6
7
Reviews: (a) D. J. Ager, I. Prakash and D. R. Schaad, Chem.
Rev., 1996, 96, 835; (b) M. M. Heravi and V. Zadsirjan,
Tetrahedron Asymmetry, 2013, 24, 1149.
Selected examples: (a) A. Huth and F. Neubauer, Liebigs Ann.
Chem., 1979, 1979, 56; (b) G. Li, R. Lenington, S. Willis and S. 17 (a) H. Lebel, K. Huard and S. Lectard, J. Am. Chem. Soc., 2005,
16 R. Singh, J. N. Kolev, P. A. Sutera and R. Fasan, ACS Catal.,
2015, 5, 1685.
Hee Kim, J. Chem. Soc., Perkin Trans. 1, 1998, 1753; (c) J. M.
Takacs, M. R. Jaber and A. S. Vellekoop, J. Org. Chem., 1998,
127, 14198; (b) K. Huard and H. Lebel, Chem. Eur. J., 2008,
14, 6222.
63, 2742; (d) G. Bratulescu, Synthesis, 2007, 2007, 3111; (e) 18 (a) H. Lebel, C. Spitz, O. Leogane, C. Trudel and M.
G. Bégis, D. E. Cladingboel, L. Jerome, W. B. Motherwell and
T. D. Sheppard, Eur. J. Org. Chem., 2009, 2009, 1532; (f) J.
Paz, C. Pérez-Balado, B. Iglesias and L. Muñoz, J. Org. Chem., 19 (a) Y. Wang, J. Wolf, P. Zavalij and M. P. Doyle, Angew.
Parmentier, Org. Lett., 2011, 13, 5460; (b) H. Lebel, C. Trudel
and C. Spitz, Chem. Commun., 2012, 48, 7799.
2010, 75, 3037; (g) S. T. Heller, T. Fu and R. Sarpong, Org.
Lett., 2012, 14, 1970; (h) N. Caldwell, P. S. Campbell, C.
Jamieson, F. Potjewyd, I. Simpson and A. J. B. Watson, J. Org.
Chem., Int. Ed., 2008, 47, 1439; (b) X. Wang, C. Weigl and M.
P. Doyle, J. Am. Chem. Soc., 2011, 133, 9572; (c) H. Lebel and
H. Piras, J. Org. Chem., 2015, 80, 3572.
Chem., 2014, 79, 9347; (i) T. He, W.-C. Gao, W.-K. Wang and 20 See supporting information for details.
C. Zhang, Adv. Synth. Catal., 2014, 356, 1113; (j) W. Mahy, P. 21 The reaction conditions were however not compatible with
K. Plucinski and C. G. Frost, Org. Lett., 2014, 16, 5020; (k) R.
unprotected nitrogen heterocycle (namely pyridine
derivative) due to a strong coordination with the rhodium
catalyst.
Mancuso, D. S. Raut, N. Della Ca, F. Fini, C. Carfagna and B.
Gabriele, ChemSusChem, 2015, 8, 2204; (l) M. Peña-López, H.
Neumann and M. Beller, Angew. Chem. Int. Ed., 2016, 55
7826.
,
22 S. Sato, M. Shibuya, N. Kanoh and Y. Iwabuchi, Chem.
Commun., 2009, 6264.
8
9
Review: G. Zappia, E. Gacs-Baitz, G. Delle Monache, D. Misiti, 23 (a) C. G. Espino, J. Du Bois, In Rhodium(II)-catalyzed oxidative
L. Nevola and B. Botta, Curr. Org. Synth., 2007,
4
, 81.
amination, Wiley-VCH Verlag GmbH & Co. KGaA: 2005; pp
379-416; (b) T. Yakura, S. Sato, Y. Yoshimoto, Chem. Pharm.
Bull. 2007, 55, 1284; (c) D. P. Uccello, S. M. Miller, N. A.
Dieterich, A. F. Stepan, S. W. Chung, K. A. Farley, B. Samas, J.
Chen, J. I. Montgomery, Tetrahedron Lett. 2011, 52, 4247; (d)
B. Hurlocker, N. C. Abascal, L. M. Repka, E. Santizo-Deleon, A.
L. Smenton, V. Baranov, R. Gupta, S. E. Bernard, S.
Chowdhury, C. M. Rojas, J. Org. Chem. 2011, 76, 2240.
Alternative Methods: (a) V. B. Birman, H. Jiang, X. Li, L. Guo
and E. W. Uffman, J. Am. Chem. Soc., 2006, 128, 6536; (b) X.
Yang, V. D. Bumbu, P. Liu, X. Li, H. Jiang, E. W. Uffman, L.
Guo, W. Zhang, X. Jiang, K. N. Houk and V. B. Birman, J. Am.
Chem. Soc., 2012, 134, 17605; (c) Q. Wang, X. Tan, Z. Zhu, X.-
Q. Dong and X. Zhang, Tetrahedron Lett., 2016, 57, 658.
10 Selected examples: (a) S. C. Bergmeier and S. J. Katz, J. Comb.
Chem., 2002,
4
, 162; (b) C. S. Park, M. S. Kim, T. B. Sim, D. K. 24 The PBE functional was selected, because it reproduces the
Pyun, C. H. Lee, D. Choi, W. K. Lee, J.-W. Chang and H.-J. Ha,
J. Org. Chem., 2003, 68, 43; (c) C. Phung and A. R. Pinhas,
Tetrahedron Lett., 2010, 51, 4552; (d) F. Fontana, C. C. Chen
and V. K. Aggarwal, Org. Lett., 2011, 13, 3454; R. A. Watile,
D. B. Bagal, Y. P. Patil and B. M. Bhanage, Tetrahedron Lett.,
2011, 52, 6383; (e) J. Seayad, A. M. Seayad, J. K. P. Ng and C.
prediction of the singlet-triplet energy difference (Est) of
dirhodium-nitrene species obtained with the more accurate
CCSD(T) method, see for example: X. F. Lin, C. Y. Zhao, C. M.
Che, Z. F. Ke and D. L. Phillips, Chem. Asian J., 2007, 2, 1101.
The full account of DFT calculations describing the energy
profile and the complete mechanism of the C-H amination is
currently under preparation: H. Lebel, E. Azek and M.
Ernzerhof, unpublished results.
L. L. Chai, ChemCatChem, 2012,
4, 774; (f) Q.-W. Song, Y.-N.
Zhao, L.-N. He, J. Gao and Z.-Z. Yang, Curr. Catal., 2012,
1
,
107; (g) A. Ueno, Y. Kayaki and T. Ikariya, Green Chem., 2013, 25 K. Huard and H. Lebel, Org. Synth., 2009, 86, 59.
14 | J. Name., 2012, 00, 1-3
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