Organic Letters
Letter
(7) (a) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116,
10075. (b) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687.
(c) Hoffmann, N. Chem. Rev. 2008, 108, 1052. (d) Vione, D.;
Maurino, V.; Minero, C.; Pelizzetti, E.; Harrison, M. A. J.; Olariu, R.-
I.; Arsene, C. Chem. Soc. Rev. 2006, 35, 441.
(8) (a) Pandey, G.; Laha, R. Angew. Chem., Int. Ed. 2015, 54, 14875.
(b) Pandey, G.; Laha, R.; Singh, D. J. Org. Chem. 2016, 81, 7161.
(9) (a) Zabicky, J. The Chemistry of Amides; Wiley-VCH: New York,
1970. (b) Greenberg, A.; Breneman, C. M. The Amide Linkage:
Structural Significance in Chemistry, Biochemistry and Material Science;
Wiley-VCH: New York, 2000. (c) Carey, J. S.; Laffan, D.; Thomson,
C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337 and references
therein.
(10) (a) Smith, M. B. Compendium of Organic Synthetic Methods, Vol.
9; John Wiley & Sons: Hoboken, NJ, 2001. (b) Swamy, K. C. K.;
Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009,
109, 2551. (c) Larock, R. C. Comprehensive Organic Transformations:
A Guide to Functional Group Preparation, Vol. 2; Wiley Blackwell: New
York, NY, 1999.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures and characterization data for
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
(11) (a) El Dine, T. M.; Erb, W.; Berhault, Y.; Rouden, J.; Blanchet,
J. J. Org. Chem. 2015, 80, 4532. (b) Hu, L.; Xu, S.; Zhao, Z.; Yang, Y.;
Peng, Z.; Yang, M.; Wang, C.; Zhao, J. J. Am. Chem. Soc. 2016, 138,
13135. (c) Cohen, I.; Mishra, A. K.; Parvari, G.; Edrei, R.; Dantus, M.;
Eichen, Y.; Szpilman, A. M. Chem. Commun. 2017, 53, 10128.
(12) Bannwart, L.; Abele, S.; Tortoioli, S. Synthesis 2016, 48, 2069.
(13) (a) Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007,
317, 790. (b) Nordstrøm, L. U.; Vogt, H.; Madsen, R. J. Am. Chem.
Soc. 2008, 130, 17672.
(14) (a) Goh, K. S.; Tan, C. H. RSC Adv. 2012, 2, 5536.
(b) Iwahana, S.; Iida, H.; Yashima, E. Chem. - Eur. J. 2011, 17, 8009.
(c) De Sarkar, S.; Studer, A. Org. Lett. 2010, 12, 1992. (d) Gaspa, S.;
Porcheddu, A.; De Luca, L. Tetrahedron Lett. 2016, 57, 3433.
(e) Allen, C. L.; Williams, J. M. Chem. Soc. Rev. 2011, 40, 3405.
(f) Tamaru, Y.; Yamada, Y.; Yoshida, Z.-I. Synthesis 1983, 1983, 474.
(15) (a) Cadoni, R.; Porcheddu, A.; Giacomelli, G.; De Luca, L. Org.
Lett. 2012, 14, 5014. (b) Zhu, M.; Fujita, K.-I.; Yamaguchi, R. J. Org.
Chem. 2012, 77, 9102. (c) Yoo, W.-J.; Li, C. J. J. Am. Chem. Soc. 2006,
128, 13064. (d) Whittaker, A. M.; Dong, V. M. Angew. Chem., Int. Ed.
2015, 54, 1312. (e) Iqbal, N.; Cho, E. J. J. Org. Chem. 2016, 81, 1905.
(16) Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions,
Mechanisms, and Structure, 6th ed.; Wiley Interscience: New York,
2007.
(17) (a) Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471.
(b) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243.
(18) Vishnyakova, T. P.; Golubeva, I. A.; Glebova, E. V. Russ. Chem.
Rev. 1985, 54, 249.
(19) (a) Kempf, D. J.; Marsh, K. C.; Paul, D. A.; Knigge, M. F.;
Norbeck, D. W.; Kohlbrenner, W. E.; Codacovi, L.; Vasavanonda, S.;
Bryant, P.; Wang, X. C.; Wideburg, N. E.; Clement, J. J.; Plattner, J. J.;
Erickson, J. Antimicrob. Agents Chemother. 1991, 35, 2209. (b) Get-
man, D. P.; DeCrescenzo, G. A.; Heintz, R. M.; Reed, K. L.; Talley, J.
J.; Bryant, M. L.; Clare, M.; Houseman, K. A.; Marr, J. J.; Mueller, R.
A.; Vazquez, M. L.; Shieh, H.-S.; Stallings, W. C.; Stegeman, R. A. J.
Med. Chem. 1993, 36, 288.
ACKNOWLEDGMENTS
■
G.P. thanks DST, New Delhi, for financial support, and S.K.
thanks DST, SERB, New Delhi. R.T. thanks CBMR, Lucknow,
and P.K.S. thanks CSIR, New Delhi for the award of a research
fellowship.
REFERENCES
■
(1) For selected recent reviews on cross-dehydrogenative coupling
reaction, see: (a) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.;
Lei, A. Chem. Rev. 2015, 115, 12138. (b) Shang, X.; Liu, Z.-Q. Chem.
Soc. Rev. 2013, 42, 3253. (c) Yeung, C. S.; Dong, V. M. Chem. Rev.
2011, 111, 1215. (d) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem.
Soc. Rev. 2011, 40, 5068. (e) Liu, C.; Zhang, H.; Shi, W.; Lei, A.
Chem. Rev. 2011, 111, 1780. (f) Ashenhurst, J. A. Chem. Soc. Rev.
2010, 39, 540. (g) Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc.
Rev. 2011, 40, 1937. (h) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
(2) (a) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed.
2014, 53, 74. (b) Scheuermann, C. Chem. - Asian J. 2010, 5, 436.
(c) Miao, J.; Ge, H. Eur. J. Org. Chem. 2015, 2015, 7859. (d) Bugaut,
X.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 7479. (e) Yang, L.;
Huang, H. Catal. Sci. Technol. 2012, 2, 1099. (f) Rohlmann, R.;
Mancheno, O. G. Synlett 2012, 24, 6. (g) Klussmann, M.;
̃
Sureshkumar, D. Synthesis 2011, 2011, 353.
(3) (a) Li, Q.; Huang, Y.; Chen, T.; Zhou, Y.; Xu, Q.; Yin, S.-F.;
Han, L.-B. Org. Lett. 2014, 16, 3672. (b) Tran, B. L.; Li, B.; Driess,
M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 2555. (c) Cheng, Y.;
Dong, W.; Wang, L.; Parthasarathy, K.; Bolm, C. Org. Lett. 2014, 16,
2000. (d) Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc.
2011, 133, 16382. (e) Sun, K.; Wang, X.; Li, G.; Zhu, Z.; Jiang, Y.;
Xiao, B. Chem. Commun. 2014, 50, 12880. (f) Krylov, I. B.; Vil’, V. A.;
Terent’ev, A. O. Beilstein J. Org. Chem. 2015, 11, 92. (g) Modak, A.;
Dutta, U.; Kancherla, R.; Maity, S.; Bhadra, M.; Mobin, S. M.; Maiti,
D. Org. Lett. 2014, 16, 2602.
(4) (a) Sarhan, A. A. O.; Bolm, C. Chem. Soc. Rev. 2009, 38, 2730.
(b) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
(c) Hirano, K.; Miura, M. Chem. Commun. 2012, 48, 10704. (d) Le
Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170. (e) Kozhushkov, S. I.;
Ackermann, L. Chem. Sci. 2013, 4, 886. (f) Patureau, F. W.; Wencel-
Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31.
(5) (a) Muramatsu, W.; Nakano, K. Org. Lett. 2015, 17, 1549.
(b) Muramatsu, W.; Nakano, K. Org. Lett. 2014, 16, 2042. (c) Mao,
L.; Li, Y.; Xiong, T.; Sun, K.; Zhang, Q. J. Org. Chem. 2013, 78, 733.
(6) (a) Amaoka, Y.; Kamijo, S.; Hoshikawa, T.; Inoue, M. J. Org.
Chem. 2012, 77, 9959. (b) Zhou, L.; Tang, S.; Qi, X.; Lin, C.; Liu, K.;
Liu, C.; Lan, Y.; Lei, A. Org. Lett. 2014, 16, 3404. (c) Michaudel, Q.;
Thevenet, D.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 2547.
(d) Jeffrey, J. L.; Bartlett, E. S.; Sarpong, R. Angew. Chem., Int. Ed.
2013, 52, 2194.
(20) (a) Hegarty, A. F.; Drennan, L. J. In Comprehensive Organic
Functional Group Transformations, Vol. 6; Katritzky, A. R., Meth-
Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; p 499.
(b) Katritzky, A. R.; Pleynet, D. P. M.; Yang, B. Z. J. Org. Chem. 1997,
62, 4155. (c) Jiang, H.; Lin, A.; Zhu, C.; Cheng, Y. Chem. Commun.
2013, 49, 819. (d) Li, X.; Li, B.; You, J.; Lan, J. Org. Biomol. Chem.
2013, 11, 1925. (e) Patil, B. S.; Vasanthakumar, G.-R.; Babu, V. V. S.
J. Org. Chem. 2003, 68, 7274. (f) King, C. J. Org. Chem. 1960, 25, 352.
(21) Kirk-Othmer, 4th ed. Encyclopaedia of Chemical Technology;
Wiley: New York, 1995; Vol. 14, p 902.
(22) Bigi, F.; Maggi, R.; Sartori, G. Green Chem. 2000, 2, 140.
(23) Mizuno, T.; Nakai, T.; Mihara, M. Synthesis 2010, 2010, 4251.
(24) Enquist, P.-A.; Nilsson, P.; Edin, J.; Larhed, M. Tetrahedron
Lett. 2005, 46, 3335.
D
Org. Lett. XXXX, XXX, XXX−XXX