10.1002/chem.201705842
Chemistry - A European Journal
FULL PAPER
[1]
a) R. J. Cremlyn, An Introduction to Organosulfur Chemistry, Wiley:
New York, 1996; b) Organosulfur Chemistry I, Ed.: P. C. B. Page,
Springer: Heidelberg, 1999; c) Organosulfur Chemistry II, Ed.: P. C. B.
Page, Springer: Heidelberg, 1999; d) C. M. Rayner, Advances in Sulfur
Chemistry, JAI Press: Greenwich, 2000, Vol. 2; e) Sulfur Compounds:
Advances in Research and Application, Ed.: A. Q. Acton, Atlanta, GA,
2012.
136, 2017; q) Q. Lu, H. Yu, Y. Fu, J. Am. Chem. Soc. 2014, 136, 8252;
r) for a related Pd-catalyzed ester to ketone reaction, see: T. B. Halima,
W. Zhang, I. Yalaoui, I.; X. Hong, Y.-F. Yang, K. N. Houk, S. G.
Newman, J. Am. Chem. Soc. 2017, 139, 1311.
[8]
For examples of Ni-catalyzed decarbonylative transformations of
amides, see: a) S. Shi, G. Meng, M. Szostak, Angew. Chem., Int. Ed.
2016, 55, 6959; b) W. Srimontree, A. Chatupheeraphat, H.-H. Liao, M.
Rueping, Org. Lett. 2017, 19, 3091; c) J. Hu, Y. Zhao, J. Liu, Y. Zhang,
Z. Shi, Angew. Chem., Int. Ed. 2016, 55, 8718; d) A. Dey, S. Sasmal, K.
Seth, G. K. Lahiri, D. Maiti, ACS Catal. 2017, 7, 433; e) Hu, J.; Wang,
M.; Pu, X.; Shi, Z. Nat. Commun. 2017, 8, 14993; f) X. Liu, H. Yue, J.
Jia, L. Guo, M. Rueping, Chem. Eur. J. 2017, 23, 11771; g) C. Liu, M.
Szostak, Angew. Chem. Int. Ed. 2017, 56, 12718; h) S.-C. Lee, L. Guo,
H. Yue, H.-H. Liao, M. Rueping, M. Synlett 2017, DOI: 10.1055/s-0036-
1591495. For examples of Pd and Rh-catalyzed decarbonylative
transformations of amides, see: i) G. Meng, M. Szostak, Angew. Chem.,
Int. Ed. 2015, 54, 14518; j) C. Liu, G. Meng, M. Szostak, J. Org. Chem.
2016, 81, 12023; k) G. Meng, M. Szostak, Org. Lett. 2016, 18, 796; l) H.
Wu, T. Liu, M. Cui, Y. Li, J. Jian, H. Wang, Z. Zeng, Org. Biomol. Chem.
2017, 15, 536; m) S. Shi, M. Szostak, Org. Lett. 2017, 19, 3095.
a) J. E. Dander, N. A. Weires, N. K. Garg, Org. Lett. 2016, 18, 3934; b)
A. C. Sather, H. G. Lee, J. R. Colombe, A. Zhang, S. L. Buchwald,
Nature 2015, 524, 208.
[2]
a) G. Liu, J. R. Huth, E. T. Olejniczak, R. Mendoza, P. DeVries, S.
Leitza, E. B. Reilly, G. F. Okasinski, S. W. Fesik, T. W. von Geldern, J.
Med. Chem. 2001, 44, 1202; b) S. W. Kaldor, V. J. Kalish, J. F. Davies,
II, B. V. Shetty, J. E. Fritz, K. Appelt, J. A. Burgess, K. M. Campanale, N.
Y. Chirgadze, D. K. Clawson, B. A. Dressman, S. D. Hatch, D. A. Khalil,
M. B. Kosa, P. P. Lubbehusen, M. A. Muesing, A. K. Patick, S. H. Reich,
K. S. Su, J. H. Tatlock, J. Med. Chem. 1997, 40, 3979; c) S. F. Nielsen,
E. O. Nielsen, G. M. Olsen, T. Liljefors, D. Peters, J. Med. Chem. 2000,
43, 2217; d) L. Liu, J. E. Stelmach, S. R. Natarajan, M.-H. Chen, S. B.
Singh, C. D. Schwartz, C. E. Fitzgerald, S. J. O’Keefe, D. M. Zaller, D.
M. Schmatz, J. B. Doherty, Bioorg. Med. Chem. Lett. 2003, 13, 3979.
For selected reviews on C-S bond formation, see: a) T. Kondo, T.-A.
Mitsudo, Chem. Rev. 2000, 100, 3205; b) I. P. Beletskaya, V. P.
Ananikov, Eur. J. Org. Chem. 2007, 3431; c) P. Bichler, J. A. Love, Top.
Organomet. Chem. 2010, 31, 39; d) C. C. Eichman, J. P. Stambuli,
Molecules 2011, 16, 590; e) A. Postigo, RSC Adv. 2011, 1, 14; f) I. P.
Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596; g) Liu, W.;
Zhao, X. Synthesis 2013, 2051; h) P. Chauhan, S. Mahajan, D. Enders,
Chem. Rev. 2014, 114, 8807; i) C.-F. Lee, Y.-C. Liu, S. S. Badsara,
Chem. Asian J. 2014, 9, 706; j) A. Sujatha, A. M. Thomas, A. P.
Thankachan, G. Anilkumar, ARKIVOC 2015, 1; k) C. Shen, P. Zhang,
Q. Sun, S. Bai, T. S. A. Hor, X. Liu, Chem. Soc. Rev. 2015, 44, 291; l) A.
Ghaderi, Tetrahedron 2016, 72, 4758; m) K. L. Dunbar, D. H. Scharf, A.
Litomska, C. Hertweck, Chem. Rev. 2017, 117, 5521.
[3]
[9]
[10] a) E. D. Scudder, R. E. Lyons, The Production of Hydrogen Sulphide by
Heating Paraffine and Other Hydrocarbon Mixtures with Sulphur, Vol.
40, Proceedings of the Indiana Academy of Science, Indiana, 1930; b)
H. A. Wiebe, A. R. Knight, O. P. Strausz, H. E. Gunning, J. Am. Chem.
Soc. 1965, 87, 1443. c) G. Schmitt, Corrosion 1991, 47, 285.
[11]
For decabonylative thioetherification of thioesters: Ni-mediated: a) E.
Wenkert, D. Chianelli, J. Chem. Soc., Chem. Commun. 1991, 9, 627;
Pd- and Rh-catalysis: b) K. Osakada, T. Yamamoto, A. Yamamoto,
Tetrahedron Lett. 1987, 28, 6321; c) T. Kato, H. Kuniyasu, T. Kajiura, Y.
Minami, A. Ohtaka, M. Kinomoto, J. Terao, H. Kurosawa, N. Kambe,
Chem. Commun. 2006, 868; for a Pd- and Ni-catalysis: d) N. Ichiishi, C.
A. Malapit, Ł. Wozniak, M. S. Sanford, Org. Lett. 2018, 20, 44.
[4]
a) B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang, A.-M.
Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111, 1346; b) S. Z.
Tasker, E. A. Standley, T. F. Jamison, Nature 2014, 509, 299; c) V. P.
Ananikov, ACS Catal. 2015, 5, 1964.
[5]
[6]
R. Takise, K. Muto, J. Yamaguchi, Chem. Soc. Rev. 2017, 46, 5864.
a) G. Meng, S. Shi, M. Szostak, Synlett 2016, 27, 2530; b) J. E. Dander,
N. K. Garg, ACS Cat. 2017, 7, 1413; c) C. Liu, M. Szostak, Chem. Eur.
J. 2017, 23, 7157.
[12] For recent use of thioesters in decarbonylative couplings, see: a) H.
Ochiai, Y. Uetake, T. Niwa, T. Hosoya, Angew. Chem. Int. Ed. 2017, 56,
2482; b) T. Niwa, H. Ochiai, M. Isoda, T. Hosoya Chem. Lett. 2017, 46,
1315.
[7]
For examples of Ni-catalyzed decarbonylative transformations of esters,
see: a) K. Amaike, K. Muto, J. Yamaguchi, K. Itami, J. Am. Chem. Soc.
2012, 134, 13573; b) A. Correa, J. Cornella, R. Martin, Angew. Chem.
Int. Ed. 2013, 52, 1878; c) L. Meng, Y. Kamada, K. Muto, J. Yamaguchi,
K. Itami, Angew. Chem., Int. Ed. 2013, 52, 10048; d) K. Muto, J.
Yamaguchi, D. G. Musaev, K. Itami, Nat. Commun. 2015, 6, 7508; e) N.
A. LaBerge, J. A. Love, Eur. J. Org. Chem. 2015, 5546; f) A. N.
Desnoyer, F. W. Friese, W. Chiu, M. W. Drover, B. O. Patrick, J. A.
Love, Chem. Eur. J. 2016, 22, 4070; g) K. Amaike, K. Itami, J.
Yamaguchi, Chem.-Eur. J. 2016, 22, 4384; h) L. Guo, A.
Chatupheeraphat, M. Rueping, Angew. Chem. Int. Ed. 2016, 55, 11810;
i) L. Guo, M. Rueping, Chem. Eur. J. 2016, 22, 16787; j) X. Pu, J. Hu, Y.
Zhao, Z. Shi, ACS Catal. 2016, 6, 6692; k) H. Yue, L. Guo, H.-H. Liao,
Y. Cai, C. Zhu, M. Rueping, Angew. Chem. Int. Ed. 2017, 56, 4282; l)
A. Chatupheeraphat, H.-H. Liao, S.-C. Lee, M. Rueping, Org. Lett. 2017,
19, 4255; m) X. Liu, J. Jia, M. Rueping, ACS Catal. 2017, 7, 4491; n) H.
Yue, L. Guo, S.-C. Lee, X. Liu, M. Rueping, Angew. Chem. Int. Ed.
2017, 56, 3972; o) R. Takise, R. Isshiki, K. Muto, K. Itami, J.
Yamaguchi, J. Am. Chem. Soc. 2017, 139, 3340; For theoretical
studies, see: p) X. Hong, Y. Liang, K. N. Houk, J. Am. Chem. Soc. 2014,
[13] a) T. Y. Zhang, J. O'Toole, C. S. Proctor, J. Sulfur Chem. 1999, 22, 1; b)
S. Yamaguchi, C. Xu, T. Okamoto, Pure Appl. Chem. 2006, 78, 721; c)
T. Yamamoto, K. Takimiya, J. Am. Chem. Soc. 2007, 129, 2224; d) J.
Schatz, T. Brendgen, D. Schühle in Comprehensive Heterocyclic
Chemistry III, Vol. 3 (Eds.: A. R. Katritzky, C. A. Ramsden, E. F. V.
Scriven, R. J. K. Taylor), Elsevier, Amsterdam, 2008, pp. 931-974; e) D.
Gramec; L. P. Mašič; M. S. Dolenc, Chem. Res. Toxicol. 2014, 27, 1344;
f) T. Liang, L. Xiao, K. Guo, W. Xu, X. Peng, Y. Cao, ACS Appl. Mater.
Interfac, 2017, 9, 7131.
[14] For selected recent examples, see: a) B. Wu, N. Yoshikai, Org. Biomol.
Chem. 2016, 14, 5402; b) E. R. Biehl, Top. Heterocycl. Chem. 2012, 29,
347; c) O. Sato, J. Nakayama in Comprehensive Heterocyclic
Chemistry III, Vol. 3 (Eds.: A. R. Katritzky, C. A. Ramsden, E. F. V.
Scriven, R. J. K. Taylor), Elsevier, Amsterdam, 2008, pp. 843-930; d) T.
Kashiki, S. Shinamura, M. Kohara, E. Miyazaki, K. Takimiya, M. Ikeda,
H. Kuwabara, Org. Lett. 2009, 11, 2473; e) B. Godoi, R. F. Shumacher,
G. Zeni, Chem. Rev. 2011, 111, 2937; f) Z. Qiao, H. Liu, X. Xiao, Y. Fu,
J. Wei, Y. Li, X. Jiang, Org. Lett. 2013, 15, 2594; g) A. J. Eberhart, H.
Shrives, Y. Zhang, A. Carrër, A. V. S. Parry, D. J. Tate, M. L. Turner, D. J.
Procter, Chem. Sci. 2016, 7, 1281.
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