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[4] T. Girihar, W. Cho, Y.H. Kim, et al., A systematic identification of efficiency
enrichment between thiazole and benzothiazole based yellow iridium(III) com-
plexes, J. Mater. Chem. 2 (2014) 9398–9405.
[5] F. Parlati, U.V. Ramesh, R.P. Singh, et al., Benzothiazole and thiazole 5,5-bipyridine
compositions and their use as ubiquitin ligase inhibitors, PCT Int. Appl. WO
2005037845, 2005.
[6] M. Yoshida, I. Hayakawa, N. Hayashi, et al., Synthesis and biological evaluation of
benzothiazole derivatives as potent antitumor agents, Bioorg. Med. Chem. Lett. 15
(2005) 3328–3332.
[7] T.R. Bailey, D.C. Pevear, Benzothiazol compounds, compositions and methods for
treatment and prophylaxis of rotavirus infections and associated diseases, PCT Int.
Appl. WO 2004078115, 2004.
[8] A. Alanine, A. Flohr, A.K. Miller, R.D. Norcross, C. Riemer, Benzothlazole deriva-
tives, PCT Int. Appl. WO 2001097786, 2001.
[9] S. Kerwin, L.H. Hurley, M.R. De, Compounds and method for providing pharma-
cologically active preparation and uses thereof, PCT Int. Appl. WO 9748694, 1997.
[10] H. Liu, X. Jiang, Transfer of sulfur: from simple to diverse, Chem. Asian J. 8 (2013)
2546–2563.
[11] D.V. Partyka, Transmetalation of unsaturated carbon nucleophiles from boron-
containing species to the mid to late block metals of relevance to catalytic C–X
coupling reactions (X = C, F, N, O, Pb, S, Se, Te), Chem. Rev. 111 (2011) 1529–1595.
[12] H. Yu, M. Zhang, Y. Li, Copper-catalyzed synthesis of benzo[b]thiophenes and
benzothiazoles using thiocarboxylic acids as a coupling partner, J. Org. Chem. 78
(2013) 8898–8903.
[13] H. Deng, Z. Li, F. Ke, X. Zhou, Cu-catalyzed three-component synthesis of substi-
tuted benzothiazoles in water, Chem. Eur. J. 18 (2012) 4840–4843.
[14] H.J. Xu, Y.Q. Zhao, T. Feng, Y.S. Feng, Chan–lam-type S-arylation of thiols with
boronic acids at room temperature, J. Org. Chem. 77 (2012) 2878–2884.
[15] D.J.C. Prasad, G. Sekar, Cu-catalyzed one-pot synthesis of unsymmetrical diaryl
thioethers by coupling of aryl halides using a thiol precursor, Org. Lett. 13 (2011)
1008–1011.
[28] C.C. Eichman, J.P. Stambuli, Zinc-mediated palladium-catalyzed formation of 276
carbon-sulfur bonds, J. Org. Chem. 74 (2009) 4005–4008.
277
[29] T. Dahl, C.W. Tornoe, B. Bang-Andersen, P. Nielsen, M. Jorgensen, Palladium- 278
catalyzed three-component approach to promazine with formation of one car- 279
bon–sulfur and two carbon–nitrogen bonds, Angew. Chem. Int. Ed. 47 (2008) 280
1726–1728.
281
[30] J.Y. Lee, P.H. Lee, Palladium-catalyzed carbon–sulfur cross-coupling reactions 282
with indium tri(organothiolate) and its application to sequential one-pot pro- 283
cesses, J. Org. Chem. 73 (2008) 7413–7426.
284
[31] M.A. Fernandez-Rodroeguez, Q. Shen, J.F. Hartwig, A general and long-lived 285
catalyst for the palladium-catalyzed coupling of aryl halides with thiols, J. Am. 286
Chem. Soc. 128 (2006) 2180–2181.
[32] M. Iwasaki, M. Iyanaga, Y. Tsuchiya, et al., Palladium-catalyzed direct thiolation of 288
aryl C–H bonds with disulfides, Chem. Eur. J. 20 (2014) 2459–2462.
287
289
[33] X.B. Xu, J. Liu, J.J. Zhang, Y.W. Wang, Y. Peng, Nickel-mediated inter- and 290
intramolecular C–S coupling of thiols and thioacetates with aryl Iodides at room 291
temperature, Org. Lett. 15 (2013) 550–553.
292
[34] N. Sakai, T. Miyazaki, T. Sakamoto, et al., Single-step thioetherification by indium- 293
catalyzed reductive coupling of carboxylic acids with thiols, Org. Lett. 14 (2012) 294
4366–4369.
[35] Y. Yang, W. Hou, L. Qin, et al., Rhodium-catalyzed directed sulfenylation of arene 296
C–H bonds, Chem. Eur. J. 20 (2014) 416–420.
295
297
[36] Y.Y. Lin, Y.J. Wang, C.H. Lin, J.H. Cheng, C.F. Lee, Synthesis of alkenyl sulfides 298
through the iron-catalyzed cross-coupling reaction of vinyl Halides with thiols, J. 299
Org. Chem. 77 (2012) 6100–6106.
[37] V.P. Reddy, K. Swapna, A.V. Kumar, K.R. Rao, Indium-catalyzed C–S cross-coupling 301
of aryl halides with thiols, J. Org. Chem. 74 (2009) 3189–3191.
300
302
[38] M. Arisawa, T. Suzuki, T. Ishikawa, M. Yamaguchi, Rhodium-catalyzed substitu- 303
tion reaction of aryl fluorides with disulfides: p-orientation in the polyarylthiola- 304
tion of polyfluorobenzenes, J. Am. Chem. Soc. 130 (2008) 12214–12215.
305
[39] Y.C. Wong, T.T. Jayanth, C.H. Cheng, Cobalt-catalyzed aryl-sulfur bond formation, 306
Org. Lett. 8 (2006) 5613–5616.
[40] H. Wang, L. Wang, J. Shang, et al., Fe-catalysed oxidative C–H functionalization/C– 308
S bond formation, Chem. Commun. 48 (2012) 76–78.
[16] L.L. Sun, C.L. Deng, R.Y. Tang, X.G. Zhang, CuI/TMEDA-catalyzed annulation of
2-bromo alkynylbenzenes with Na2S: synthesis of benzo[b]thiophenes, J. Org.
Chem. 76 (2011) 7546–7550.
[17] H.L. Kao, C.F. Lee, Efficient copper-catalyzed s-vinylation of thiols with vinyl
halides, Org. Lett. 13 (2011) 5204–5207.
[18] F. Ke, Y. Qu, Z. Jiang, et al., An efficient copper-catalyzed carbon-sulfur bond
formation protocol in water, Org. Lett. 13 (2011) 454–457.
[19] D. Chen, Z.J. Wang, W. Bao, Copper-catalyzed cascade syntheses of 2H-ben-
307
309
[41] Y. Cheng, J. Yang, Y. Qu, P. Li, Aerobic visible-light photoredox radical C–H 310
functionalization: catalytic synthesis of 2-substituted benzothiazoles, Org. Lett. 311
14 (2012) 98–101.
[42] F. Jia, Z.P. Li, Iron-catalyzed/mediated oxidative transformation of C–H bonds, Org. 313
Chem. Front. 1 (2014) 194–214.
[43] L. Chu, X. Yue, F.L. Qing, Cu(II)-mediated methylthiolation of aryl C–H bonds with 315
DMSO, Org. Lett. 12 (2010) 1644–1647.
312
314
zo[b][1,4]thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing
S
and N atom respectively from AcSH and TsNH2, J. Org. Chem. 75 (2010) 5768–5771.
[20] C.L. Li, X.G. Zhang, R.Y. Tang, P. Zhong, J.H. Li, Copper-catalyzed thiolation
annulations of 1,4-dihalides with sulfides leading to 2-trifluoromethyl benzothio-
phenes and benzothiazoles, J. Org. Chem. 75 (2010) 7037–7040.
[21] W. You, X. Yan, Q. Liao, C. Xi, Cu-catalyzed double s-alkenylation of potassium
sulfide: a highly efficient method for the synthesis of various thiophenes, Org.
Lett. 12 (2010) 3930–3933.
[22] Y. Jiang, S. Xie, Y. Qin, X. Zhang, D. Ma, A general and efficient approach to aryl
thiols: CuI-catalyzed coupling of aryl lodides with sulfur and subsequent reduc-
tion, Org. Lett. 11 (2009) 5250–5253.
[23] S. Murru, P. Mondal, R. Yella, B.K. Patel, Copper(I)-catalyzed cascade synthesis of
2-substituted 1,3-benzothiazoles: direct access to benzothiazolones, Eur. J. Org.
Chem. (2009) 5406–5413.
[24] S. Murru, H. Ghosh, S.K. Sahoo, B.K. Patel, Intra- and intermolecular C–S bond
formation using a single catalytic system: first direct access to arylthiobenzothia-
zoles, Org. Lett. 11 (2009) 4254–4257.
[25] C.G. Bates, P. Saejueng, M.Q. Doherty, D. Venkataraman, Copper-catalyzed
synthesis of vinyl sulfides 6 (2004) 5005–5008.
[26] Z. Qiao, H. Liu, X. Xiao, et al., Efficient access to 1,4-benzothiazine: palladium-
catalyzed double C–S bond formation using Na2S2O3 as sulfurating reagent, Org.
Lett. 15 (2013) 2594–2597.
[27] M. Kuhn, F.C. Falk, J. Paradies, Palladium-catalyzed C–S coupling: access to
thioethers, benzo[b]thiophenes, and thieno[3,2-b]thiophenes, Org. Lett. 13
(2011) 4100–4103.
316
[44] X. Zhang, W. Zeng, Y. Yang, H. Huang, Y. Liang, Copper-catalyzed double C–S 317
bonds formation via different paths: synthesis of benzothiazoles from N-benzyl- 318
2-iodoaniline and potassium sulfide, Org. Lett. 16 (2014) 876–879.
319
[45] K. Inamoto, Y. Arai, K. Hiroya, T. Doi, Palladium-catalysed direct synthesis of 320
benzo[b]thiophenes from thioenols, Chem. Commun. 43 (2008) 5529–5531.
321
[46] K. Inamoto, C. Hasegawa, K. Hiroya, T. Doi, Palladium-catalyzed synthesis of 322
2-substituted benzothiazoles via a C–H functionalization/intramolecular C–S 323
bond formation process, Org. Lett. 10 (2008) 5147–5150.
324
[47] J.K. Wang, F. Peng, J.L. Jiang, et al., Synthesis of N-benzothiazol-2-yl-amides by a 325
copper-catalyzed intramolecular cyclization process, Tetrahedron Lett. 49 (2008) 326
467–470.
327
[48] J.K. Wang, Y.X. Zong, Y.X. Zhang, et al., Synthesis of N-benzothiazol-2-yl-amides 328
by
Fe-catalyzed oxidative C(sp2)–H functionalization, Synlett 25 (2014) 329
2143–2148.
a
330
[49] X.C. Wang, Z. Li, Y. Tu, Y.X. Da, Synthesis of N-(5-aryloxymethyl-1,3,4-thiadiazol-2- 331
yl)-N0-(5-aryl-2-furoyl)-thioureas under phase transfer catalysis, Synth. Commun. 332
32 (2002) 1113–1119.
333
[50] Z. Li, X.C. Wang, Synthesis of 1-aryloxyacetyl-4-(4-nitrobenzoyl)-thiosemicarab- 334
zides under phase transfer catalysis and microwave irradiation, Synth. Commun. 335
32 (2002) 3087–3092.
336
[51] K. Inamoto, T. Saito, M. Katsuno, T. Sakamoto, K. Hiroya, Palladium-catalyzed C–H 337
activation/intramolecular amination reaction: a new route to 3-aryl/alkylinda- 338
zoles, Org. Lett. 9 (2007) 2931–2934.
339
275
Please cite this article in press as: J.-K. Wang, et al., Synthesis of N-benzothiazol-2-yl-amides by Pd-catalyzed C(sp2)–H