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Organic & Biomolecular Chemistry
Page 4 of 5
COMMUNICATION
Journal Name
excellent yields under unusually mild and energy-wise reaction
conditions. Preliminary mechanistic investigations revealed
J. Am. Chem. Soc., 2013, 135, 1823; (j)DGO. IB: 1.0D.1e0n3g9,/CZ6.OQB.0W06a1n7Eg,
J. D. Xia, P. C. Qian, R. J. Song, M. Hu, L. B. Gong and J. H. Li,
Angew. Chem. Int. Ed., 2013, 52, 1535; (k) S. Cai, S. L. Zhang,
Y. Zhao and D. Z. Wang, Org. Lett., 2013, 15, 2660; (l) P. Kohls,
D. Jadhav, G. Pandey and O. Reiser, Org. Lett., 2012, 14, 672;
that
a radical pathway was possibly involved in this
transformation. Further studies on this reaction mechanism,
reaction scope, and synthetic application will thus be
continuously pursued in our laboratory and the results will be
disclosed in due course.
(m) Z. Lu and T. P. Yoon, Angew. Chem. Int. Ed., 2012, 51
10329.
,
6
(a) S. Cai, X. Zhao, X. Wang, Q. Liu, Z. Li and D. Z. Wang,
Angew. Chem. Int. Ed., 2012, 51, 8050; (b) S. Maity, M. Z. Zhu,
R. S. Shinabery and N. Zheng, Angew. Chem. Int. Ed., 2012,
51, 222; (c) Y. Zou, J. Chen, X. Liu, L. Lu, R. Davis, K. A.
Acknowledgements
The work is supported by the National Natural Science
Foundation of China (No. 21502086 and No. 41575118),
Natural Science Foundation of Fujian Province (No.
2015J05028), Outstanding Youth Science Foundation of Fujian
Province (No. 2015J06009), and Program for Excellent Talents
of Minnan Normal University (MJ14005). We also thank Prof.
David Zhigang Wang (Peking University) for helpful discussions.
Jorgensen and W. J. Xiao, Angew. Chem. Int. Ed., 2012, 51
,
784; (d) D. A. DiRocco and T. Rovis, J. Am. Chem. Soc., 2012,
134, 8094; (e) M. A. Ischay, M. S. Ament and T. P. Yoon,
Chem. Sci., 2012, 3, 2807; (f) S. Lin, M. A. Ischay, C. G. Fry and
T. P. Yoon, J. Am. Chem. Soc., 2011, 133, 19350; (i) C. Dai, J.
M. R. Narayanam and C. R. J. Stephenson, Nature Chem.,
2011,
3, 140; (j) A. McNally, C. K. Prier and D. W. C.
MacMillan, Science, 2011, 334, 1114; (k) Y. Q. Zou, L. Q. Lu, L.
Fu, N. J. Chang, J. Rong, J. R. Chen and W. J. Xiao, Angew.
Chem. Int. Ed., 2011, 50, 7171; (l) D. Kalyani, K. B. McMurtrey,
S. R. Neufeldt and M. S. Sanford, J. Am. Chem. Soc., 2011,
133, 18566; (m) M. Rueping, D. Leonori and T. Poisson, Chem.
Commun., 2011, 47, 9615; (n) J. D. Nguyen, J. W. Tucker, M.
D. Konieczynska and C. R. J. Stephenson, J. Am. Chem. Soc.,
2011, 133, 4160; (o) D. A. Nagib and D. W. C. MacMillan,
Nature, 2011, 480, 224.
Notes and references
1
(a) C. Curti, M. Laget, A. O. Carle, A. Gellis and P. Vanelle, Eur.
J. Med. Chem., 2007, 42, 880; (b) H. Yang, R. G. Carter and L.
N. Zakharov, J. Am. Chem. Soc., 2008, 130, 9238; (c) M.
Artico, R. Silvestri, E. Pagnozzi, B. Bruno, E. Novellino, G.
Greco, S. Massa, A. Ettorre, A. G. Loi, F. Scintu and P. L. Coll, J.
Med. Chem., 2000, 43, 1886; (d) J. L. Marco, J. Org. Chem.,
1997, 62, 6575.
(a) G. E. Vennstra and B. Zwaneburg, Synthesis 1975, 519; (b)
Y.-Y. Xie and Z.-C. Chen, Synth. Commun., 2001, 31, 3145; (c)
A. R. Katritzky, A. A. Abdel-Fattah and M. Y. Wang, J. Org.
Chem., 2003, 68, 1443; (d) B. M. Trost and D. P. Curran,
Tetrahedron Lett., 1981, 22, 1287; (e) N. Samakkanad, P.
Katrun, T. Techajaroonjit, S. Hlekhlai, M. Pohmakotr, V.
Reutrakul, T. Jaipetch, D. Soorukram and C. Kuhakarn,
Synthesis, 2012, 1693.
7
(a) C. J. Wallentin, J. D. Nguyen, P. Finkbeiner and C. R. J.
Stephenson, J. Am. Chem. Soc., 2012, 134, 8875; (b) J. W.
Tucker and C. R. J. Stephenson, Org. Lett. 2011, 13, 5468; (c)
R. S. Andrews, J. J. Becker and M. R. Gagné, Angew. Chem.
Int. Ed., 2010, 49, 7274; (d) J. W. Tucker, J. D. Nguyen, J. M. R.
Narayanam, S. W. Krabbe and C. R. J. Stephenson, Chem.
Commun., 2010, 46, 4985; (e) H. W. Shih, M. N. Vander Wal,
R. L. Grange and D. W. C. MacMillan, J. Am. Chem. Soc., 2010,
132, 13600; (f) A. G. Condie, J. C. González-Gómez and C. R. J.
Stephenson, J. Am. Chem. Soc., 2010, 132, 1464; (g) M. A.
2
Ischay, Z. Lu and T. P. Yoon, J. Am. Chem. Soc., 2010, 132
8572; (h) J. Du and T. P. Yoon, J. Am. Chem. Soc., 2009, 131
,
,
3
(a) Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang and A. W. Lei, J.
Am. Chem. Soc., 2013, 135, 11481; (b) W. Wei, C. Liu, D. Yang,
J. Wen, J. You, Y. Suo and H. Wang, Chem. Commun., 2013,
49, 10239; (c) A. K. Singh, R. Chawla and L. D. S. Yadav,
Tetrahedron Lett., 2014, 55, 4742; (d) X. Tang, L. Huang, Y. Xu,
14604; (i) D. A. Nicewicz and D. W. C. MacMillan, Science,
2008, 322, 77.
8
9
(a) Q. Lu, J. Zhang, F. Wei, Y. Qi, H. Wang, Z. Liu and A. W. Lei,
Angew. Chem. Int. Ed., 2013, 52, 7156; (b) X. Li, X. Xu, P. Hu,
X. Xiao and C. Zhou, J. Org. Chem., 2013, 78, 7343.
For instructive uses of KI in organic synthesis, see: (a) S. Tang,
Y. Wu, W. Liao, R. Bai, C. Liu and A. W. Lei, Chem. Commun.,
2014, 50, 4496; (b) P. Katrun, S. Chiampanichayakul, K.
Korworapan, M. Pohmakotr, V. Reutrakul and T. Jaipetch, C.
Kuhakarn, Eur. J. Org. Chem., 2010, 5633.
J. Yang, W. Wu and H. Jiang, Angew. Chem. Int. Ed., 2014, 53
4205; (e) V. S. Rawat, P. L. M. Reddy and B. Sreedhar, RSC
Adv., 2014, , 5165; (f) A. K. Singh, R. Chawla, T. Keshari, V. K.
,
4
Yadav and L. D. S. Yadav, Org. Biomol. Chem., 2014, 12, 8550.
(g) H. Jiang, Y. Cheng, Y. Zhang and S. Yu, Eur. J. Org. Chem.,
2013, 5485.
4
5
For selected reviews on photo-redox catalysis, see: (a) T. P.
10 (a) D. P. Hari and B. nig, Org. Lett., 2011, 13, 3852; (b) M.
Neumann, S. ldner, B. nig and K. Zeitler, Angew. Chem.
Int. Ed., 2011, 50, 951; (c) D. Cantillo, O. de Frutos, J. A.
inc n, C. Mateos and C. O. Kappe, Org. Lett., 2014, 16, 896;
(d) Q. Y. Meng, J. J. Zhong, Q. Liu, X. W. Gao, H. H. Zhang, T.
Lei, Z. J. Li, K. Feng, B. Chen, C. H. Tung and L. Z. Wu, J. Am.
Chem. Soc., 2013, 135, 19052.
Yoon, M. A. Ischay and J. Du, Nat. Chem., 2010, 2, 527; (b) J.
M. R. Narayanam and C. R. J. Stephenson, Chem. Soc. Rev.,
2011, 40, 102; (c) J. Xuan and W.-J. Xiao, Angew. Chem. Int.
Ed., 2012, 51, 6828; (d) C. K. Prier, D. A. Rankic and D. W. C.
MacMillan, Chem. Rev., 2013, 113, 5322; (e) D. M. Schultz
and T. P. Yoon, Science, 2014, 343,985; (f) D. Ravelli, D. Dondi,
M. Fagnoni and A. Albini, Chem. Soc. Rev., 2009, 38, 1999.
(a) Q.-Q. Zhou, W. Guo, W. Ding, X. Wu, Xi. Chen, L.-Q. Lu
and W.-J. Xiao, Angew. Chem. Int. Ed., 2015, 54, 11196; (b) A.
U. Meyer, S. Jager, D. P. Hari and B. K nig, Adv. Synth. Catal.,
2015, 357, 2050; (c) J. Du, K. L. Skubi, D. M. Schultz and T. P.
Yoon, Science, 2014, 344, 392; (d) J. D. Nguyen, B. S.
Matsuura and C. R. J. Stephenson, J. Am. Chem. Soc., 2014,
136, 1218; (e) A. Noble and D. W. C. MacMillan, J. Am. Chem.
Soc., 2014, 136, 11602; (f) W. G. Fan and P. X. Li, Angew.
Chem. Int. Ed., 2014, 53, 12201; (g) E. Arceo, E. Montroni and
P. Melchiorre, Angew. Chem. Int. Ed., 2014, 53, 12064; (h) S.
Cai, K. Yang and D. Z. Wang, Org. Lett., 2014, 16, 2606; (i) S.
11 (a) X. Li, X. Xu and X. Shi, Tetrahedron Lett., 2013, 54, 3071;
(b) V. Nair, A. Augustine and T. D. Suja, Synthesis, 2002, 2259;
(c) A. Kariya, T. Yamaguchi, T. Nobuta, N. Tada, T. Miura and
A. Itoh, RSC Adv., 2014, 4, 13191.
12 (a) R. Singh, B. K. Allam, N. Singh, K. Kumari, S. K. Singh and K.
N. Singh, Org. Lett., 2015, 17, 2656; (b) S. Handa, J. C.
Fennewald and B. H. Lipshutz, Angew. Chem. Int. Ed., 2014,
53, 3432.
13 For visible-light-enabled iodine radical formation, see: (a) J.
M. Gardner, M. Abrahamsson, B. H. Farnum and G. J. Meyer,
4 | J. Name., 2012, 00, 1-3
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