Organic Letters
Letter
J. Synth. Org. Chem., Jpn 2016, 74, 1119. (f) Otsuka, S.; Nogi, K.;
Yorimitsu, H. Top. Curr. Chem. 2018, 376, 13.
(4) (a) Miura, M.; Itoh, K.; Nomura, M. Chem. Lett. 1989, 18, 77.
(b) Li, X.; Liang, D.; Huang, W.; Zhou, H.; Li, Z.; Wang, B.; Ma, Y.;
Wang, H. Tetrahedron 2016, 72, 8442.
2-methoxyethanol or phenols to C would be enhanced with
the aid of their methoxy group or π-systems as additional
coordination sites. Indeed, competition reaction revealed that
m-cresol (2k) reacted much faster than 1-butanol (2a) to
provide 3bk in 87% yield (Scheme 7).
(5) Kamigata, N.; Satoh, A.; Yoshida, M.; Kameyama, M. Bull. Chem.
Soc. Jpn. 1989, 62, 605.
Scheme 7. Competition Reaction between 2a and 2k
(6) Shim, S. C.; Antebi, S.; Alper, H. J. Org. Chem. 1985, 50, 147.
(7) (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G.
Principles and Applications of Organotransition Metal Chemistry;
University Science Books: Sausalito, CA, 1987; Chapters 3.6a and
12. (b) Hocking, R. K.; Hambley, T. W. Organometallics 2007, 26,
2815.
(8) (a) Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc.
1997, 119, 12376. (b) Zhang, S.; Marshall, D.; Liebeskind, L. S. J. Org.
Chem. 1999, 64, 2796.
(9) Review: Tian, Z.-Y.; Hu, Y.-T.; Teng, H.-B.; Zhang, C.-P.
Tetrahedron Lett. 2018, 59, 299.
(10) (a) Vasu, D.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed.
2015, 54, 7162. (b) Vasu, D.; Yorimitsu, H.; Osuka, A. Synthesis 2015,
In conclusion, we have developed palladium-catalyzed
alkoxycarbonylation of aryldimethylsulfoniums under an
atmospheric pressure of CO. With characteristic reactivity of
organosulfur compounds, the present alkoxycarbonylation will
open up a new way of utilizing carbonylative transformations
of organosulfur compounds.
̈
47, 3286. (c) Cowper, P.; Jin, Y.; Turton, M. D.; Kociok-Kohn, G.;
Lewis, S. E. Angew. Chem., Int. Ed. 2016, 55, 2564. (d) Wang, X.-Y.;
Song, H.-X.; Wang, S.-M.; Yang, J.; Qin, H.-L.; Jiang, X.; Zhang, C.-P.
Tetrahedron 2016, 72, 7606. (e) Wang, S.-M.; Wang, X.-Y.; Qin, H.-
L.; Zhang, C.-P. Chem. - Eur. J. 2016, 22, 6542. (f) Kawashima, H.;
Yanagi, T.; Wu, C.-C.; Nogi, K.; Yorimitsu, H. Org. Lett. 2017, 19,
ASSOCIATED CONTENT
* Supporting Information
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S
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4552. (g) Cowper, P.; Pockett, A.; Kociok-Kohn, G.; Cameron, P. J.;
The Supporting Information is available free of charge on the
Lewis, S. E. Tetrahedron 2018, 74, 2775. Arylation of
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alkenylsulfoniums: (h) Hooper, J. F.; Chaplin, A. B.; Gonzalez-
Rodríguez, C.; Thompson, A. L.; Weller, A. S.; Willis, M. C. J. Am.
Chem. Soc. 2012, 134, 2906. (i) Lin, H.; Dong, X.; Li, Y.; Shen, Q.;
Lu, L. Eur. J. Org. Chem. 2012, 2012, 4675. (j) Aukland, M. H.;
Detailed experimental procedures, and full spectroscopic
data for all new compounds (PDF)
́
Talbot, F. J. T.; Fernandez-Salas, J. A.; Ball, M.; Pulis, A. P.; Procter,
D. J. Angew. Chem., Int. Ed. 2018, 57, 9785. Arylation of
AUTHOR INFORMATION
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benzylsulfoniums: (k) Vanier, C.; Lorge, F.; Wagner, A.;
Corresponding Author
ORCID
Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679.
(11) (a) Wang, S.-M.; Song, H.-X.; Wang, X.-Y.; Liu, N.; Qin, H.-L.;
Zhang, C.-P. Chem. Commun. 2016, 52, 11893. (b) Uno, D.; Minami,
H.; Otsuka, S.; Nogi, K.; Yorimitsu, H. Chem. - Asian J. 2018, 13,
2397.
Notes
(12) Tian, Z.-Y.; Wang, S.-M.; Jia, S.-J.; Song, H.-X.; Zhang, C.-P.
Org. Lett. 2017, 19, 5454.
The authors declare no competing financial interest.
(13) (a) Minami, H.; Otsuka, S.; Nogi, K.; Yorimitsu, H. ACS Catal.
2018, 8, 579. (b) Minami, H.; Nogi, K.; Yorimitsu, H. Heterocycles
2018, 97, 998.
ACKNOWLEDGMENTS
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(14) (a) Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc.
This work was supported by JSPS KAKENHI Grant Numbers
JP16H04109, JP18H04254, JP18H04409, and JP18K14212.
H.Y. thanks The Asahi Glass Foundation for financial support.
̈
1989, 111, 8742. (b) Magerlein, W.; Indolese, A. F.; Beller, M. Angew.
̈
Chem., Int. Ed. 2001, 40, 2856. (c) Beller, M.; Magerlein, W.;
̈
Indolese, A. F.; Fischer, C. Synthesis 2001, 2001, 1098. (d) Magerlein,
W.; Indolese, A. F.; Beller, M. J. Organomet. Chem. 2002, 641, 30.
(e) Beller, M.; Zapf, A. In Handbook of Organopalladium Chemistry for
Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: Hoboken, NJ,
2002.
(15) Bruno, N. C.; Niljianskul, N.; Buchwald, S. L. J. Org. Chem.
2014, 79, 4161.
(16) (a) Chekal, B.; Damon, D.; Lafrance, D.; Leeman, K.; Mojica,
C.; Palm, A.; St. Pierre, M.; Sieser, J.; Sutherland, K.; Vaidyanathan,
R.; Van Alsten, J.; Vanderplas, B.; Wager, C.; Weisenburger, G.;
Withbroe, G.; Yu, S. Org. Process Res. Dev. 2015, 19, 1944. (b) Lee, Y.
H.; Morandi, B. Nat. Chem. 2018, 10, 1016.
(17) van Leeuwen, P. W. N. M.; Zuideveld, M. A.; Swennenhuis, B.
H. G.; Freixa, Z.; Kamer, P. C. J.; Goubitz, K.; Fraanje, J.; Lutz, M.;
Spek, A. L. J. Am. Chem. Soc. 2003, 125, 5523.
(18) (a) Kubota, Y.; Nakada, S.; Sugi, Y. Synlett 1998, 1998, 183.
(b) Cai, C.; Rivera, N. R.; Balsells, J.; Sidler, R. R.; McWilliams, J. C.;
Shultz, C. S.; Sun, Y. Org. Lett. 2006, 8, 5161. (c) Munday, R. H.;
Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 2754.
REFERENCES
■
(1) Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39,
3318.
(2) Reviews: (a) Beller, M.; Wu, X.-F. Hydroxy-, Alkoxy-, and
Aminocarbonylations of C−X Bonds. In Transition Metal Catalyzed
Carbonylation Reactions; Beller, M., Wu, X.-F., Eds.; Springer: Berlin,
Heidelberg, 2013; pp 13−52. (b) Barnard, C. F. J. Organometallics
2008, 27, 5402. (c) Brennfuhrer, A.; Neumann, H.; Beller, M. Angew.
̈
Chem., Int. Ed. 2009, 48, 4114. (d) Feng, X.; Tomiyasu, H.; Hu, J.-Y.;
Wei, X.; Redshaw, C.; Elsegood, M. R. J.; Horsburgh, L.; Teat, S. J.;
Yamato, T. J. Org. Chem. 2015, 80, 10973. (e) Gautam, P.; Bhanage,
B. M. Catal. Sci. Technol. 2015, 5, 4663.
(3) Reviews on transition-metal-catalyzed coupling reactions via C−
S cleavage: (a) Dubbaka, S. R.; Vogel, P. Angew. Chem., Int. Ed. 2005,
44, 7674. (b) Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599.
(c) Modha, S. G.; Mehta, V. P.; van der Eycken, E. V. Chem. Soc. Rev.
2013, 42, 5042. (d) Pan, F.; Shi, Z.-J. ACS Catal. 2014, 4, 280.
(e) Gao, K.; Otsuka, S.; Baralle, A.; Nogi, K.; Yorimitsu, H.; Osuka, A.
D
Org. Lett. XXXX, XXX, XXX−XXX