Organic Letters
Letter
(e) Kayser, H.; Eilinger, P. Pest Manage. Sci. 2001, 57, 975. (f) Wang, B.
L.; Zhu, H. W.; Ma, Y.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.;
Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483.
(4) Reviews: (a) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107,
5713. (b) Chauhan, P.; Mahajan, S.; Enders, D. Chem. Rev. 2014, 114,
8807. For selected examples: (c) Inokuma, T.; Hoashi, Y.; Takemoto, Y.
J. Am. Chem. Soc. 2006, 128, 9413. (d) Sibi, M. P.; Itoh, K. J. Am. Chem.
Soc. 2007, 129, 8064. (e) Zhang, Y.; Liu, Y. K.; Kang, T. R.; Hu, Z. K.;
Chen, Y. C. J. Am. Chem. Soc. 2008, 130, 2456. (f) Zhao, Q.; Wen, J.;
Tan, R.; Huang, K.; Metola, P.; Wang, R.; Anslyn, E. V.; Zhang, X.
isothiocyanate 7d, which demonstrated that isothiocyanate could
be formed in the reaction (Scheme 3, eq 3).
In summary, we have developed an efficient and practical
thiocarbonyl surrogate for the construction of various
thiocarbamides and oxazolidinethiones via combination of sulfur
and chloroform. Moreover, the procedure was successfully
applied for the establishment of chiral thiourea catalysts, chiral
oxazolidinethione auxiliaries, and a commercial pesticides library.
Further studies on other thiocarbonyl surrogates are ongoing in
our laboratory.
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z, A.; Dosa, Z.; Varga,
Angew. Chem., Int. Ed. 2014, 53, 8467. (h) Madaras
S.; Soos, T.; Csampai, A.; Papai, I. ACS Catal. 2016, 6, 4379.
(5) (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
(b) Velazquez, F.; Olivo, H. F. Curr. Org. Chem. 2002, 6, 303.
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ASSOCIATED CONTENT
* Supporting Information
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(c) Sakamoto, M. In Comprehensive Chirality; Carreira, E. M.,
Yamamoto, H., Eds.; Elsevier B.V.: Amsterdam, The Netherlands,
2012; Vol. 3, pp 19−41.
The Supporting Information is available free of charge on the
(6) (a) Yella, R.; Ghosh, H.; Patel, B. K. Green Chem. 2008, 10, 1307.
Experimental procedures, NMR spectral, X-ray, and
analytical data for all new compounds (PDF)
Crystallographic data (CIF)
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(b) Cano, I.; Gomez-Bengoa, E.; Landa, A.; Maestro, M.; Mielgo, A.;
Olaizola, I.; Oiarbide, M.; Palomo, C. Angew. Chem., Int. Ed. 2012, 51,
10856. (c) Zhao, J.; Huang, H.; Wu, W.; Chen, H.; Jiang, H. Org. Lett.
2013, 15, 2604. (d) Appalanaidu, K.; Dadmal, T.; Babu, N. J.;
Kumbhare, R. M. RSC Adv. 2015, 5, 88063.
AUTHOR INFORMATION
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(7) Reviews: (a) Schroeder, D. C. Chem. Rev. 1955, 55, 181. (b) Staab,
H. A. Angew. Chem., Int. Ed. Engl. 1962, 1, 351. (c) Sharma, S. Synthesis
1978, 1978, 803. (d) Ortiz, A.; Sansinenea, E. J. Sulfur Chem. 2007, 28,
109. (e) Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210.
(f) Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2010, 110, 3419. For
selected examples: (g) Ballabeni, M.; Ballini, R.; Bigi, F.; Maggi, R.;
Parrini, M.; Predieri, G.; Sartori, G. J. Org. Chem. 1999, 64, 1029.
(h) Katritzky, A. R.; Ledoux, S.; Witek, R. M.; Nair, S. K. J. Org. Chem.
2004, 69, 2976. (i) Maddani, M. R.; Prabhu, K. R. J. Org. Chem. 2010, 75,
2327. (j) Chau, C. M.; Chuan, T. J.; Liu, K. M. RSC Adv. 2014, 4, 1276.
(8) Reviews: (a) Liu, H.; Jiang, X. Chem. - Asian J. 2013, 8, 2546.
(b) Feng, M.; Tang, B.; Liang, S.; Jiang, X. Curr. Top. Med. Chem. 2016,
16, 1200. (c) Qiao, Z.; Jiang, X. Org. Biomol. Chem. 2017, 15, 1942. For
representative examples: (d) Qiao, Z.; Liu, H.; Xiao, X.; Fu, Y.; Wei, J.;
Li, Y.; Jiang, X. Org. Lett. 2013, 15, 2594. (e) Qiao, Z.; Wei, J.; Jiang, X.
Org. Lett. 2014, 16, 1212. (f) Li, Y.; Pu, J.; Jiang, X. Org. Lett. 2014, 16,
2692. (g) Zhang, Y.; Li, Y.; Zhang, X.; Jiang, X. Chem. Commun. 2015,
51, 941. (h) Qiao, Z.; Ge, N.; Jiang, X. Chem. Commun. 2015, 51, 10295.
(i) Xiao, X.; Feng, M.; Jiang, X. Chem. Commun. 2015, 51, 4208. (j) Li,
Y.; Xie, W.; Jiang, X. Chem. - Eur. J. 2015, 21, 16059. (k) Qiao, Z.; Jiang,
X. Org. Lett. 2016, 18, 1550. (l) Wang, M.; Fan, Q.; Jiang, X. Org. Lett.
2016, 18, 5756. (m) Xiao, X.; Feng, M.; Jiang, X. Angew. Chem., Int. Ed.
2016, 55, 14121. (n) Wang, M.; Wei, J.; Fan, Q.; Jiang, X. Chem.
Commun. 2017, 53, 2918.
(9) Wei, J.; Li, Y.; Jiang, X. Org. Lett. 2016, 18, 340.
́
(10) Fedorynski, M. Chem. Rev. 2003, 103, 1099.
(11) (a) Gockel, S. N.; Hull, K. L. Org. Lett. 2015, 17, 3236. (b) Liu, X.;
Li, B.; Gu, Z. J. Org. Chem. 2015, 80, 7547. (c) Zhao, H.; Du, H.; Yuan,
X.; Wang, T.; Han, W. Green Chem. 2016, 18, 5782. (d) Sun, G.; Lei, M.;
Hu, L. RSC Adv. 2016, 6, 28442.
(12) (a) Meyer, B. Chem. Rev. 1976, 76, 367. (b) Boyd, D. A. Angew.
Chem., Int. Ed. 2016, 55, 2.
(13) (a) Huang, J.; Schanz, H. J.; Stevens, E. D.; Nolan, S. P. Inorg.
Chem. 2000, 39, 1042. (b) Takikawa, Y.; Yamaguchi, M.; Sasaki, T.;
Ohnishi, K.; Shimada, K. Chem. Lett. 1994, 23, 2105.
(14) (a) Weber, W. P.; Gokel, G. W. Tetrahedron Lett. 1972, 13, 1637.
(b) Lipp, M.; Dallacker, F.; zu Kocker, I. M. Monatsh. Chem. 1959, 90,
41. (c) Weith, W. Chem. Ber. 1873, 6, 212. (d) Hofmann, A. W. Ann.
Chem. 1867, 144, 114.
(15) CCDC-1524792 (5g) contains the supplementary crystallo-
graphic data for this paper. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via www.ccdc.cam.
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful for financial support provided by NSFC
(21672069, 21472050), DFMEC (20130076110023), Fok
Ying Tung Education Foundation (141011), Program for
Shanghai Rising Star (15QA1401800), Professor of Special
Appointment (Eastern Scholar) at Shanghai Institutions of
Higher Learning, and the National Program for Support of Top-
notch Young Professionals.
REFERENCES
■
(1) Reviews: (a) Butler, I. S. Acc. Chem. Res. 1977, 10, 359.
(b) Maciejewski, A.; Steer, R. P. Chem. Rev. 1993, 93, 67. (c) Sakamoto,
M. In Topics in Current Chemistry; Toda, F., Ed.; Springer: Berlin,
Heidelberg, 2005; Vol. 254, pp 207−232. (d) Li, A. F.; Wang, J. H.;
Wang, F.; Jiang, Y. B. Chem. Soc. Rev. 2010, 39, 3729. (e) Sahu, S.; Sahoo,
P. R.; Patel, S.; Mishra, B. K. J. Sulfur Chem. 2011, 32, 171.
́
(2) Reviews: (a) Rodríguez-Fernandez, E.; Manzano, J. L.; Benito, J. J.;
Hermosa, R.; Monte, E.; Criado, J. J. J. Inorg. Biochem. 2005, 99, 1558.
(b) D’Cruz, O. J.; Uckun, F. M. Curr. HIV Res. 2006, 4, 329. (c) Manna,
D.; Roy, G.; Mugesh, G. Acc. Chem. Res. 2013, 46, 2706. For selected
examples: (d) Weiss, M.; Buhl, R.; Medve, M.; Schneider, E. M. Crit.
Care Med. 1997, 25, 128. (e) Harper, L.; Chin, L.; Daykin, J.;
Allahabadia, A.; Heward, J.; Gough, S. C.; Savage, C. O.; Franklyn, J. A.
Clin. Endocrinol. 2004, 60, 671. (f) Van Daele, I. V.; Munier-Lehmann,
H.; Froeyen, M.; Balzarini, J.; Van Calenbergh, S. V. J. Med. Chem. 2007,
́
50, 5281. (g) Touati-Jallabe, Y.; Bojnik, E.; Legrand, B.; Mauchauffee, E.;
Chung, N. N.; Schiller, P. W.; Benyhe, S.; Averlant-Petit, M. C.;
Martinez, J.; Hernandez, J. F. J. Med. Chem. 2013, 56, 5964. (h) Ma, L.
Y.; Zheng, Y. C.; Wang, S. Q.; Wang, B.; Wang, Z. R.; Pang, L. P.; Zhang,
M.; Wang, J. W.; Ding, L.; Li, J.; Wang, C.; Hu, B.; Liu, Y.; Zhang, X. D.;
Wang, J. J.; Wang, Z. J.; Zhao, W.; Liu, H. M. J. Med. Chem. 2015, 58,
1705.
(3) For selected examples: (a) Gaines, T. B.; Hayes, W. J., Jr. Public
Health Rep. 1952, 67, 306. (b) Gratz, N. G. Bull. World Health Organ.
1973, 48, 469. (c) Schuntner, C. A.; Thompson, P. G. Pestic. Sci. 1979,
10, 519. (d) Pascual, A.; Rindlisbacher, A. Pestic. Sci. 1994, 42, 253.
(16) (a) Prasad, K. D. 2001 US 6303787 B1. (b) Gangula, S.; Elati, C.
R.; Neredla, A.; Baddam, S. R.; Neelam, U. K.; Bandichhor, R.;
Dongamanti, A. Org. Process Res. Dev. 2010, 14, 229.
D
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