Organic Letters
Letter
́
́
(2) (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
(b) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282.
(c) Reissig, H. U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
(d) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326. (e) Smith, A.
B.; Adams, C. M. Acc. Chem. Res. 2004, 37, 365. (f) Ballini, R.; Bosica,
G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.
(g) Chatterjee, A.; Joshi, N. N. Tetrahedron 2006, 62, 12137.
(h) Guo, F.; Clift, M. D.; Thomson, R. J. Eur. J. Org. Chem. 2012,
2012, 4881. (i) Nakajima, M.; Fava, E.; Loescher, S.; Jiang, Z.;
Rueping, M. Angew. Chem., Int. Ed. 2015, 54, 8828.
(3) (a) Ahlbrecht, H.; Beyer, U. Synthesis 1999, 1999, 365.
(b) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107,
5606. (c) Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37,
2691. (d) Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.;
Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336. (e) Menon, R.
S.; Biju, A. T.; Nair, V. Chem. Soc. Rev. 2015, 44, 5040.
(d) Gutierrez-Bonet, A.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.;
Molander, G. A. ACS Catal. 2016, 6, 8004. (e) Nakajima, K.; Nojima,
S.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2016, 55, 14106.
(f) Huang, W.; Cheng, X. Synlett 2017, 28, 148.
(15) For an example of a reductive radical coupling of unactivated
olefins with conjugate acceptors, see: Lo, J. C.; Yabe, Y.; Baran, P. S. A
Practical and Catalytic Reductive Olefin Coupling. J. Am. Chem. Soc.
2014, 136, 1304−1307.
(16) A preliminary investigation of chiral ligands has yielded a
promising 68:32 e.r. in 41% isolated yield using Feng’s ramipirl
derived N-oxide ligand. See SI for details. With the same dimethyl
benzylic radical, Melchiorre et al. reported 46% yield, 71% ee for the
alkylation of cinnaldehyde (ref 9c).
(17) (a) Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C.
Nature 2012, 492, 234. (b) Luo, J.; Zhang, J. ACS Catal. 2016, 6, 873.
(18) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
(19) Full conversion of (2-,3-,4-) pyridine and quinoline derived
AMs heteroarylidene malonates was observed with no identifiable
products.
(20) (a) Espelt, L. R.; McPherson, I. S.; Wiensch, E. M.; Yoon, T. P.
J. Am. Chem. Soc. 2015, 137, 2452. (b) Huo, H.; Harms, K.; Meggers,
E. J. Am. Chem. Soc. 2016, 138, 6936.
(21) Zhou, Z. J.; Li, Y. J.; Han, B. W.; Gong, L.; Meggers, E. Chem.
Sci. 2017, 8, 5757.
(22) Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426.
(23) Elinson, M. N.; Feducovich, S. K.; Zakharenkov, A. A.; Ugrak,
B. I.; Nikishin, G. I.; Lindeman, S. V.; Struchkov, J. T. Tetrahedron
1995, 51, 5035.
(24) Cao, Y.; Zhang, S. C.; Zhang, M.; Shen, G. B.; Zhu, X. Q. J. Org.
Chem. 2013, 78, 7154.
(25) Mizuno, K.; Nakanishi, K.; Chosa, J.; Otsuji, Y. J. Organomet.
Chem. 1994, 473, 35.
(4) Claisen, L. Justus Liebigs Annalen der Chemie 1876, 180, 1.
(5) Danly, D. E. J. Electrochem. Soc. 1984, 131, 435C.
(6) (a) Streuff, J. Chem. - Eur. J. 2011, 17, 5507. (b) Streuff, J.
Synthesis 2013, 45, 281. (c) Bichovski, P.; Haas, T. M.; Keller, M.;
Streuff, J. Org. Biomol. Chem. 2016, 14, 5673.
(7) (a) Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785. (b) Yoon,
T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527. (c) Narayanam, J.
M. R.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102. (d) Xuan, J.;
Xiao, W. Angew. Chem., Int. Ed. 2012, 51, 6828. (e) Ravelli, D.;
Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97. (f) Prier, C. K.;
Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
(g) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016,
81, 6898. (h) Nakajima, K.; Miyake, Y.; Nishibayashi, Y. Acc. Chem.
Res. 2016, 49, 1946. (i) Bloom, S.; Liu, C.; Kolmel, D. K.; Qiao, J. X.;
Zhang, Y.; Poss, M. A.; Ewing, W. R.; MacMillan, D. W. C. Nat. Chem.
2017, 10, 205.
(8) (a) Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am.
Chem. Soc. 2008, 130, 12886. (b) Du, J.; Yoon, T. P. J. Am. Chem. Soc.
2009, 131, 14604. (c) Du, J.; Espelt, L. R.; Guzei, I. A.; Yoon, T. P.
Chem. Sci. 2011, 2, 2115. (d) Hurtley, A. E.; Cismesia, M. A.; Ischay,
M. A.; Yoon, T. P. Tetrahedron 2011, 67, 4442. (e) Amador, A. G.;
Sherbrook, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2016, 138, 4722.
(f) Yoon, T. P. Acc. Chem. Res. 2016, 49, 2307. (g) Skubi, K. L.; Blum,
T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
(26) Zhao, G.; Yang, C.; Guo, L.; Sun, H.; Lin, R.; Xia, W. J. Org.
Chem. 2012, 77, 6302.
(27) (a) Yamashita, M.; Okuyama, K.; Kawasaki, I.; Nakamura, S.;
Nagamine, R.; Tsujita, T.; Ohta, S. Chem. Pharm. Bull. 2000, 48, 1799.
(b) Kise, N.; Iitaka, S.; Iwasaki, K.; Ueda, N. J. Org. Chem. 2002, 67,
8305.
(9) (a) Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc.
2013, 135, 10022. (b) Miller, D. C.; Choi, G. J.; Orbe, H. S.;
Knowles, R. R. J. Am. Chem. Soc. 2015, 137, 13492. (c) Tarantino, K.
T.; Miller, D. C.; Callon, T. A.; Knowles, R. R. J. Am. Chem. Soc. 2015,
137, 6440. (d) Jeffrey, J. L.; Terrett, J. A.; MacMillan, D. W. C. Science
2015, 349, 1532. (e) Yayla, H. G.; Wang, H.; Tarantino, K. T.; Orbe,
H. S.; Knowles, R. R. J. Am. Chem. Soc. 2016, 138, 10794. (f) Choi, G.
J.; Zhu, Q.; Miller, D. C.; Gu, C. J.; Knowles, R. R. Nature 2016, 539,
268. (g) Lee, K. N.; Lei, Z.; Ngai, M. Y. J. Am. Chem. Soc. 2017, 139,
5003. (h) Zhou, Z.; Li, Y.; Han, B. W.; Gong, L.; Meggers, E. Chem.
Sci. 2017, 8, 5757.
(10) (a) Murphy, J. J.; Bastida, D.; Paria, S.; Fagnoni, M.;
Melchiorre, P. Nature 2016, 532, 218. (b) Dell’Amico, L.;
Fernandez-Alvarez, V. M.; Maseras, F.; Melchiorre, P. Angew. Chem.,
Int. Ed. 2017, 56, 3304. (c) Silvi, M.; Verrier, C.; Rey, Y. P.; Buzzetti,
L.; Melchiorre, P. Nat. Chem. 2017, 9, 868. (d) Verrier, C.; Alandini,
N.; Pezzetta, C.; Moliterno, M.; Buzzetti, L.; Hepburn, H. B.; Vega-
Penaloza, A.; Silvi, M.; Melchiorre, P. ACS Catal. 2018, 8, 1062.
(11) Lo, J. C.; Yabe, Y.; Baran, P. S. J. Am. Chem. Soc. 2014, 136,
1304.
(12) Gang, D.; Jun, Y.; Xiao-ping, Y.; Hui-jun, X. Tetrahedron 1990,
46, 5967.
(13) Shono, T.; Nishiguchi, I.; Ohmizu, H. J. Am. Chem. Soc. 1977,
99, 7396.
́
́ ́
(14) (a) Nunez-Vergara, L. J.; Lopez-Alarcon, C.; Navarrete-Encina,
̃
P. A.; Atria, A. M.; Camargo, C.; Squella, J. A. Free Radical Res. 2003,
37, 109. (b) Li, G.; Chen, R.; Wu, L.; Fu, Q.; Zhang, X.; Tang, Z.
Angew. Chem., Int. Ed. 2013, 52, 8432. (c) Chen, W.; Liu, Z.; Tian, J.;
Li, J.; Ma, J.; Cheng, X.; Li, G. J. Am. Chem. Soc. 2016, 138, 12312.
E
Org. Lett. XXXX, XXX, XXX−XXX