Journal of the American Chemical Society
Communication
(13) (a) Carreno, M. C.; Gonzal
́
ez-Lop
́
ez, M.; Urbano, A. Chem.
̃
notion that this new strategy for the synthesis of polyaromatic
hydrocarbons does indeed proceed via oxetanes as reactive
intermediates.18
Commun. 2005, 5, 611. (b) Liu, L.; Katz, T. J. Tetrahedron Lett. 1990, 31,
3983. (c) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A.
L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119,
10054. (d) Fox, J. M.; Goldberg, N. R.; Katz, T. J. J. Org. Chem. 1998, 63,
7456. (e) Dreher, S. D.; Weix, D. J.; Katz, T. J. J. Org. Chem. 1999, 64,
3671.
(14) (a) Harrowven, D. C.; Guy, I. L.; Nanson, L. Angew. Chem., Int.
Ed. 2006, 45, 2242. (b) Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D.
R. Tetrahedron Lett. 2002, 43, 7345.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
(15) For examples, see: (a) Furstner, A.; Mamane, V. J. Org. Chem.
̈
2002, 67, 6264. (b) Mamane, V.; Hannen, P.; Furstner, A. Chem. - Eur. J.
̈
2004, 10, 4556. (c) Komeyama, K.; Igawa, R.; Takaki, K. Chem.
Commun. 2010, 46, 1748. (d) Chernyak, N.; Gevorgyan, V. J. Am. Chem.
Soc. 2008, 130, 5636. (e) Chernyak, N.; Gevorgyan, V. Adv. Synth. Catal.
2009, 351, 1101.
(16) Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J.
Angew. Chem., Int. Ed. 2012, 51, 5714.
(17) (a) Iuliano, A.; Piccioli, P.; Fabbri, D. Org. Lett. 2004, 6, 3711.
(b) Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem., Int. Ed. 2006,
45, 2664.
AUTHOR INFORMATION
Corresponding Author
■
(18) (a) This work was first reported as Ludwig, J. R.; Gianino, J. B.;
Schindler, C. Metal-catalyzed carbonyl−olefin metathesis. Abstracts of
Papers, 250th ACS National Meeting & Exposition, Boston, MA, August
16−20, 2015; American Chemical Society: Washington, DC, 2015;
1328933, ORGN-447. (b) Ludwig, J. R.; Zimmerman, P. M.; Gianino, J.
B.; Schindler, C. S. Nature 2016, 533, 374.
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
(19) For metal-mediated carbonyl−olefin metathesis reactions, see:
(a) Schopov, I.; Jossifov, C. Makromol. Chem., Rapid Commun. 1983, 4,
659. (b) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800. For
carbonyl−olefin metathesis reactions proceeding via oxetan photo-
adducts, see: (c) Jones, G., II; Schwartz, S. B.; Marton, M. T. J. Chem.
Soc., Chem. Commun. 1973, 11, 374. (d) Jones, G., II; Acquadro, M. A.;
Carmody, M. A. J. Chem. Soc., Chem. Commun. 1975, 6, 206. (e) Carless,
H. A. J.; Trivedi, H. S. J. Chem. Soc., Chem. Commun. 1979, 8, 382.
(f) D’Auria, M.; Racioppi, R.; Viggiani, L. Photochem. Photobiol. Sci.
■
We thank the Petroleum Research Fund (PRF#54688-DNI1),
the University of Michigan Office of Research, the NIH/
National Institute of General Medical Sciences (GM118644)
and the David and Lucile Packard Foundation for financial
support. P.S.R. thanks Eli Lilly for a summer predoctoral
fellowship. We thank Dr. Jeff W. Kampf and Ren Wiscons for X-
ray crystallographic studies.
2010, 9, 1134. (g) Per
2005, 70, 1376. (h) Per
́
ez-Ruiz, R.; Gil, S.; Miranda, M. A. J. Org. Chem.
́
ez-Ruiz, R.; Miranda, M. A.; Alle, R.; Meerholz,
REFERENCES
■
K.; Griesbeck, A. G. Photochem. Photobiol. Sci. 2006, 5, 51. (i) Valiulin,
R. A.; Arisco, T. M.; Kutateladze, A. G. J. Org. Chem. 2011, 76, 1319.
(j) Valiulin, R. A.; Arisco, T. M.; Kutateladze, A. G. J. Org. Chem. 2013,
78, 2012. For Brønsted and Lewis acid mediated carbonyl−olefin
(1) (a) Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH:
New York, 1997. (b) Gingras, M. Chem. Soc. Rev. 2013, 42, 968.
(c) Gingras, M.; Felix, G.; Peresutti, R. Chem. Soc. Rev. 2013, 42, 1007.
(d) Gingras, M. Chem. Soc. Rev. 2013, 42, 1051. (e) Floyd, A. J.; Dyke, S.
F.; Ward, S. E. Chem. Rev. 1976, 76, 509. For additional examples, see:
(f) Uchida, K.; Ito, S.; Nakano, M.; Abe, M.; Kubo, T. J. Am. Chem. Soc.
2016, 138, 2399. (g) Ji, F.; Li, X.; Wu, W.; Jiang, H. J. Org. Chem. 2014,
79, 11246.
(2) Wigglesworth, T. J.; Sud, D.; Norsten, T. B.; Lekhi, V. S.; Branda,
N. R. J. Am. Chem. Soc. 2005, 127, 7272.
(3) Furche, F.; Ahlrichs, R.; Wachsmann, C.; Weber, E.; Sobanski, A.;
Vogtle, F.; Grimme, S. J. Am. Chem. Soc. 2000, 122, 1717.
(4) Xu, Y.; Zhang, Y. X.; Sugiyama, H.; Umano, T.; Osuga, H.; Tanaka,
K. J. Am. Chem. Soc. 2004, 126, 6566.
metathesis reactions, see: (k) Soicke, A.; Slavov, N.; Neudorfl, J.-M.;
̈
Schmalz, H.-G. Synlett 2011, 2011, 2487. (l) van Schaik, H.-P.; Vijn, R.-
J.; Bickelhaupt, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1611. (m) Bah,
J.; Franzen, J.; Naidu, V. R. Eur. J. Org. Chem. 2015, 2015, 1834.
́
(n) Jossifov, C.; Kalinova, R.; Demonceau, A. Chim. Oggi 2008, 26, 85.
For catalytic carbonyl−olefin metathesis reactions proceeding via
(3+2)/retro-(3 + 2)-cycloaddition, see: (o) Griffith, A. K.; Vanos, C.
M.; Lambert, T. H. J. Am. Chem. Soc. 2012, 134, 18581. (p) Hong, X.;
Liang, Y.; Griffith, A. K.; Lambert, T. H.; Houk, K. N. Chem. Sci. 2014, 5,
471.
̈
(20) (a) Satchell, D. P. N.; Satchell, R. S. Chem. Rev. 1969, 69, 251.
(b) Jensen, W. B. Chem. Rev. 1978, 78, 1.
(21) Kepp, K. P. Inorg. Chem. 2016, 55, 9461.
(22) In the carbonyl−olefin metathesis reaction leading to cyclo-
pentenes and cyclohexenes, catalytic amounts of BF3·Et2O formed the
metathesis products in 71% (86% conversion).
(5) (a) Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998,
120, 264. (b) Zophel, L.; Enkelmann, V.; Mullen, K. Org. Lett. 2013, 15,
̈
̈
804.
(6) Kovacs, A.; Vasas, A.; Hohmann, J. Phytochemistry 2008, 69, 1084.
(7) For representative examples, see: (a) Knowles, R. R.; Lin, S.;
Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030. (b) Narcis, M. J.;
Takenaka, N. Eur. J. Org. Chem. 2014, 1, 21.
(8) Dreher, S. D.; Katz, T. J.; Lam, K.-C.; Rheingold, A. L. J. Org. Chem.
2000, 65, 815.
(9) McMurry, J. E.; Lectka, T.; Rico, J. G. J. Org. Chem. 1989, 54, 3748.
(10) Dubois, F.; Gingras, M. Tetrahedron Lett. 1998, 39, 5039.
(11) (a) Flammang-Barbieux, M.; Nasielski, J.; Martin, R. H.
Tetrahedron Lett. 1967, 8, 743. (b) Liu, L.; Yang, B.; Katz, T. J.;
Poindexter, M. K. J. Org. Chem. 1991, 56, 3769. (c) Martin, R. H. Angew.
Chem., Int. Ed. Engl. 1974, 13, 649.
(23) Arnai
(24) (a) Sanz, R.; Fernan
Fananas, F. J. J. Org. Chem. 2006, 71, 6291. (b) Che, R.; Wu, Z.; Li, Z.;
́
z, F. J. J. Chem. Educ. 1995, 72, 1139.
́
dez, Y.; Castroviejo, M. P.; Perez, A.;
́
́
̃
Xiang, H.; Zhou, X. Chem. - Eur. J. 2014, 20, 7258. (c) Qiao, Z.; Ge, N.;
Jiang, X. Chem. Commun. 2015, 51, 10295.
(12) For homolytic aromatic substitution strategy, see: Harrowven, D.
C.; Guy, I. L.; Nanson, L. Angew. Chem., Int. Ed. 2006, 45, 2242.
D
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX