Journal of the American Chemical Society
Communication
Han, Z.; Gallou, I. Aldrichimica Acta 2005, 38, 93. (e) Zhou, P.; Chen,
B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
(4) For the Rh(III)-catalyzed intermolecular addition of non-acidic
C−H bonds to imines, see: (a) Zhou, B.; Yang, Y.; Lin, S.; Li, Y. Adv.
Synth. Catal. 2013, 355, 360. (b) Tauchert, M. E.; Incarvito, C. D.;
Rheingold, A. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2012,
134, 1482. (c) Li, Y.; Zhang, X.-S.; Li, H.; Wang, W.-H.; Chen, K.; Li,
B.-J.; Shi, Z.-J. Chem. Sci. 2012, 3, 1634. (d) Li, Y.; Zhang, X.-S.; Zhu,
Q.-L.; Shi, Z.-J. Org. Lett. 2012, 14, 4498. (e) Hesp, K. D.; Bergman, R.
G.; Ellman, J. A. Org. Lett. 2012, 14, 2304. (f) Li, Y.; Li, B.-J.; Wang,
W.-H.; Huang, W.-P.; Zhang, X.-S.; Chen, K.; Shi, Z.-J. Angew. Chem.,
Int. Ed. 2011, 50, 2115. (g) Tsai, A. S.; Tauchert, M. E.; Bergman, R.
G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 1248.
(5) For cobalt-catalyzed intermolecular addition of non-acidic C−H
bonds to imines, see: (a) Yoshino, T.; Ikemoto, H.; Matsunaga, S.;
Kanai, M. Chem.Eur. J. 2013, 19, 9142. (b) Yoshino, T.; Ikemoto,
H.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 2207.
(c) Gao, K.; Yoshikai, N. Chem. Commun. 2012, 48, 4305.
(6) For recent reviews on Rh(III)-catalyzed C−H functionalization,
see: (a) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(b) Patureau, F. W.; Wencel-Delord, J.; Glorius, F. Aldrichimica Acta
2012, 45, 31. (c) Satoh, T.; Miura, M. Chem.Eur. J. 2010, 16, 11212.
(7) For the asymmetric synthesis of diarylmethanamines by Pd-
catalyzed C−H iodination, see: Chu, L.; Wang, X.-C.; Moore, C. E.;
Rheingold, A. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344.
(8) For catalytic enantioselective cascade reactions that involve
intramolecular C−H bond addition to imine directing groups, see:
(a) Nishimura, T.; Nagamoto, M.; Ebe, Y.; Hayashi, T. Chem. Sci.
2013, 4, 4499. (b) Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed.
2011, 50, 11098.
(9) For asymmetric Rh(III)-catalyzed addition of C−H bond to
alkenes and allenes using chiral catalysts, see: (a) Ye, B.; Donets, P. A.;
Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 507. (b) Ye, B.; Cramer,
N. J. Am. Chem. Soc. 2013, 135, 636. (c) Hyster, T. K.; Knorr, L.;
̈
Ward, T. R.; Rovis, T. Science 2012, 338, 500. (d) Ye, B.; Cramer, N.
Science 2012, 338, 504.
(10) For previous reports on the preparation, good stability, and
reagent additions to N-perfluorinated sulfinyl imines, see: (a) Kai, Y.;
Liu, L.-J.; Liu, J.-T. J. Org. Chem. 2014, 79, 3215. (b) Liu, L.-J.; Liu, J.-
T. Tetrahedron 2014, 70, 1236. (c) Liu, Z.-J.; Zhang, F.; Liu, J.-T. J.
Fluorine Chem. 2012, 133, 102. (d) Liu, L.-J.; Chen, L.-J.; Li, P.; Li, X.-
B.; Liu, J.-T. J. Org. Chem. 2011, 76, 4675. (e) Li, P.; Liu, L.-J.; Liu, J.-
T. Org. Biomol. Chem. 2011, 9, 74.
(11) For Rh(III)-catalyzed C−H functionalization of azobenzenes
other than imine addition, see: (a) Wang, H.; Yu, Y.; Hong, X.; Tan,
Q.; Xu, B. J. Org. Chem. 2014, 79, 3279. (b) Lian, Y.; Hummel, J. R.;
Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 12548.
(c) Muralirajan, K.; Cheng, C. H. Chem.Eur. J. 2013, 19, 6198.
(d) Lian, Y.; Bergman, R. G.; Lavis, L. D.; Ellman, J. A. J. Am. Chem.
Soc. 2013, 135, 7122.
(12) An authentic mixture of diastereomers was prepared by methods
previously reported for tert-butanesulfinyl imine addition products:
Brak, K.; Barrett, K. T.; Ellman, J. A. J. Org. Chem. 2009, 74, 3606.
(13) Li, L.; Brennessel, W.; Jones, W. D. Organometallics 2009, 28,
3492.
(14) X-ray structures have been determined for seven-membered
rhodacycles obtained upon addition of 2-phenylpyridine to N-
carbamoyl and N-sulfonyl imines. For each class of imine, the nitrogen
and an oxygen of the nitrogen substituent were both observed to be
coordinated to the cationic rhodium center. See refs 4b,c.
D
dx.doi.org/10.1021/ja5033452 | J. Am. Chem. Soc. XXXX, XXX, XXX−XXX