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Org aP nl ei ca s &e dB oi o nmo to al ed cj uu sl at rm Ca hr ge imn si stry
Journal Name
ARTICLE
Rev. 2010, 111, 1293; (d) H. M. L. Davies, J. Du Bois and J.-Q.
DOI: 10.1039/C6OB01243D
Yu, Chem. Soc. Rev., 2011, 40, 1855 and references therein;
(
e) W. C. P. Tsang, N. Zheng and S. L. Buchwald, J. Am. Chem.
Soc. 2005, 127, 14560; (f) B. Zhang and A. Studer, Chem. Soc.
Rev. 2015, 44, 3505. (g) X. Liu, B. Sun, Z. Xie, X. Qin, L. Liu and
H. Lou, J. Org. Chem., 2013, 78, 3104; (h) Z. Meng, S. Sun, H.
Yuan, H. Lou and L. Liu, Angew. Chem. Int. Ed. 2014, 53, 543.
For selected publications and review on CDC reactions, see:
2
(
a) Z. Li and C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968; (b) Z.
Li and C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672; (c) C.-J. Li,
Acc. Chem. Res. 2009, 42, 335; (d) S. A. Girard, T. Knauber
and C.-J. Li, Angew. Chem., Int. Ed. 2014, 53, 74; (e) C. S.
Yeung and V. M. Dong, Chem. Rev. 2011, 111, 1215; (f) C. Liu,
H. Zhang, W. Shi and A. Lei, Chem. Rev. 2011, 111, 1780; (g)
Z. Xie, Lei Liu, W. Chen, H. Zheng, Q. Xu, H. Yuan and H. Lou
Angew. Chem. Int. Ed. 2014, 53, 3904; (h) W. Chen, Z. Xie, H.
Zheng, H. Lou and L. Liu Org. Lett. 2014, 16, 5988; (i) M.
Wan, Z. Meng, H. Lou and L. Liu Angew. Chem. Int. Ed. 2014,
53, 13845.
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4
T. Kondo and T.a. Mitsudo, Chem. Rev. 2000, 100, 3205.
For application of α-sulfenyl monoketones see the following
selected reviews and publications: (a) B. M. Trost, Chem.
Rev. 1978, 78, 363; (b) P. Chauhan, S. Mahajan and D.
Enders, Chem. Rev. 2014, 114, 8807 and references therein;
For Olefination reactions, see (c) S. Hok and N. E. Schore, J.
Org. Chem. 2006, 71, 1736; (d) A. Kumar, S. Sharma, V. D.
Tripathi and S. Srivastava, Tetrahedron 2010, 66, 9445; For β-
keto sulfones see (e) H. Loghmani-Khouzani and D.
Hajiheidari, J. Fluor. Chem., 2010, 131, 561; (f) M.-Y. Chang,
Y.-C. Cheng and Y.-J. Lu, Org. Lett. 2014, 16, 6252; (g) M. T.
Saraiva, G. P. Costa, N. Seus, R. F. Schumacher, G. Perin, M.
W. Paixao, R. Luque, D. Alves, Org. Lett. 2015, 17, 6206. For
bioactive compounds, see (h) S. Chitra, N. Paul, S.
Muthusubramanian, P. Manisankar, P. Yogeeswari and D.
Sriram, Eur. J. Med. Chem., 2011, 46, 4897 and references
therein; For application of α-sulfenyl monoketones in
asymmetric synthesis, see (i) M. W. Paixão, N. Holub, C. Vila,
M. Nielsen and K. A. Jørgensen, Angew. Chem., Int. Ed. 2009,
Scheme 3: Proposed mechanism
Conclusion
In conclusion, we have developed an operationally simple and
straightforward method for synthesizing α-sulfenyl ketones via
cross dehydrogenative coupling (CDC) and demonstrated a
broad substrate scope. Also, in the case of propiophenones
and many other aliphatic ketones, the reaction has the
potential to be developed into an enantioselective reaction.
Therefore, we believe that these sulfenylation reactions under
CDC conditions would be attractive alternatives for C-S bond-
forming reactions and find applications in organic synthesis.
Further investigations are underway in our laboratory to
generate chiral α-sulfenyl ketones.
4
8, 7338; (j) N. Holub, H. Jiang, M. W. Paixão, C. Tiberi and K.
A. Jørgensen, Chem. Eur. J. 2010, 16, 4337. (k) Q.-G. Wang,
Q.-Q. Zhou, J.-G. Deng and Y.- C. Chen, Org. Lett. 2013, 15,
4786.
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6
(a) B. M. Trost, T. N. Salzmann and K. Hiroi, J. Am. Chem. Soc.
1
976, 98, 4887; application in natural product synthesis: (b)
J. H. Rigby, M. S. Laxmisha, A. R. Hudson, C. H. Heap and M. J.
Heeg, J. Org. Chem. 2004, 69, 6751; (c) J. Chun, G. Li, H. Byun
and R. Bittman, J. Org. Chem. 2002, 67, 2600; (d) T. Guney
and G. A. Kraus, Org. Lett. 2013, 15, 613.
Selected publications from our laboratory; (a) J.
Dhineshkumar, M. Lamani, K. Alagiri and K. R. Prabhu, Org.
Lett. 2013, 15, 1092; (b) K. Alagiri and K. R. Prabhu, Org.
Biomol. Chem. 2012, 10, 835–842; (c) M. Lamani and K. R.
Prabhu, J. Org. Chem. 2011, 76, 7938; (d) M. Lamani and K. R.
Prabhu, Chem. Eur. J. 2012, 18, 14638; (e) J. Dhineshkumar
and K. R. Prabhu, Org. Lett. 2013, 15, 6062; (f) K. Alagiri, G. S.
R. Kumara and K. R. Prabhu, Chem. Commun. 2011, 47,
Acknowledgements
The financial supports from IISc, SERB (NO.SB/S1/OC-56/2013),
New Delhi, and CSIR (No. 02(0226)15/EMR-II), New Delhi are
gratefully acknowledged. Authors thank Dr. Ramesha, A. R. (RL
Fine Chem) for useful discussion. B. V. V. Thanks CSIR for a
senior fellowship.
1
1787; (g) K. Alagiri, P. Devadig and K. R. Prabhu, Chem.Eur.
J. 2012, 18, 5160–5164.
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(a) R. Otto and A. Rossing, Ber. 1890, 23,756; (b) F. Asinger,
M. Thiel and i. Kalzendorf, Justus Liebigs Ann. Chem., 1957,
6
10, 25; (c) F. Asinger, W. Schafer and H. Triem, Monatsh.
Chem.. 1966, 97,1510; (d) W. E. Truce and R. Knospe, J. Am.
Notes and references
Chem. Soc. 1955, 77, 5063.
1
For selected publications and review on C−H bond
functionalization reactions, see: (a) H. M. L. Davies and D.
Morton, J. Org. Chem. 2016, 81, 343; (b) D. Seidel, Acc.
Chem. Res. 2015, 48, 317; (c) K. Godula and D. Sames,
(a) S. Sengupta and S. Mondal, Tetrahedron Lett. 1999, 40,
8685; (b) L.-H. Zou, D. L. Priebbenow, L. Wang, J. Mottweiler,
C. Bolm, Adv. Synth. Catal. 2013, 355, 2558.
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