Journal of the American Chemical Society
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Ohshiro, Y.; Agawa, T. Synthesis 1981, 56. (c) Hirao, T.;
Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull.
Chem. Soc. Jpn. 1982, 55, 909.
N. Angew. Chem. Int. Ed. 2010, 49, 2929. (d) Mesganaw, T.;
Silberstein, A. L.; Ramgren, S. D.; Nathel, N. F. F.; Hong, X.;
Liu, P.; Garg, N. K. Chem. Sci. 2011, 2, 1766. (e) Huang, K.;
Yu, D.-G.; Zheng, S.-F.; Wu, Z.-H.; Shi, Z.-J. Chem. Eur. J.
2011, 17, 786. (f) Hie, L.; Ramgren, S. D.; Mesganaw, T.;
Garg, N. K. Org. Lett. 2012, 14, 4182.
(6) Hirao`s process has been studied and modified extensively:
(a) Jablonkai, E.; Keglevich, G. Tetrahedron Lett. 2013, 54,
4185. (b) Berger, O.; Petit, C., Dea,l E. L.; Montchamp J.-L.
Adv. Synth. Catal. 2013, 355, 1361. (c) Xu, Y.; Li, Z.; Xia, J.;
Guo, H.; Huang, Y. Synthesis 1984, 781. (d) Kazankova, M.
A.; Trostyanskaya, I. G.; Lutsenko, S. V.; Beletskaya, I. P.
Tetrahedron Lett. 1999, 40, 569. (e) Stelzer, O.; Sheldrick,
W. S. J. Organomet. Chem. 2002, 645, 14. (e) Pirat, J.-L.;
Monbrun, J.; Virieux, D.; Cristau, H.-J. Tetrahedron 2005,
61, 7029. (f) Belabassi, Y.; Alzghari, S.; Montchamp, J.-L. J.
Organometallic Chem. 2008, 693, 3171. (g) Deal, E. L.; Petit,
C.; Montchamp, J.-L. Org. Lett. 2011, 13, 3270. (h) Rum-
melt, S. M.; Ranocchiari, M.; van Bokhoven, J. A. Org. Lett.
2012, 14, 2188.
(11) Other examples see: (a) Correa, A.; León, T.; Martin, R. J.
Am. Chem. Soc. 2014, 136, 1062. (b) Álvarez-Bercedo, P.;
Martin, R. J. Am. Chem. Soc. 2010, 132, 17352. (c) Tobisu,
M.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Chem.
Commun. 2011, 47, 2946.
(12) 3a’ could be quantitatively oxidized to 3a upon heating under
air. It was thought that 3’ was probably generated from the
cross coupling of naphthyl pivalate 1a with Ph2PH which
was formed by the disproportionation of diphenylphosphine
oxide.
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(13) The reactions of the corresponding PhOC(O)t-Bu and related,
however, progressed sluggishly under similar conditions and
produced low yields of the products (ca.10%).
(7) Palladium-catalyzed coupling of the highly reactive triflates
with P(O)–H compounds is known. Holt, D. A.; Erb, J. M.
Tetrahedron Lett. 1989, 30, 5393.
(14) (a) Muto, K.; Yamaguchi, J.; Lei, A.; Itami, K. J. Am. Chem.
Soc. 2013, 135, 16384. (b) Xu, H.; Muto, K.; Yamaguchi, J.;
Zhao, C.; Itami, K.; Musaev, D. G. J. Am. Chem. Soc. 2014,
136, 14834. (c) Takise, R.; Muto, K.; Yamaguchi, J.; Itami,
K. Angew. Chem. Int. Ed. 2014, 53, 6791.
(8) Transition metal-catalyzed activation of C–O bonds for the
construct carbon-carbon bonds is attracted much attention.
The construction of a carbon-heteroatom is limited. For
reviews, see (a) Yamaguchi, J.; Muto, K.; Itami, K. Eur. J.
Org. Chem., 2013, 19. (b) Tasker, S. Z.; Standley, E. A.;
Jamison, T. F. Nature, 2014, 509, 299. (c) Cornella, J.;
Zarate, C.; Martin, R. Chem. Soc. Rev., 2014, 43, 8081. (d)
Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.;
Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev., 2011,
111, 1346. (e) Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res.
2010, 43, 1486. (f) Tobisu, M.; Chatani, N. Top Organomet.
Chem. 2013, 44, 35.
(9) Contributions to C–C bond formation via C–O activation
have been made by Shi, Garg, Itami, Martin and others: (a)
Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem.
Soc. 1979, 101, 2246. (b) Wenkert, E.; Michelotti, E. L.;
Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894. (c)
Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem. Int. Ed.
2008, 47, 4866. (d) Yu, D.-G.; Shi, Z.-J. Angew. Chem. Int.
Ed. 2011, 50, 7097. (e) Quasdorf, K. W.; Antoft-Finch, A.;
Liu, P.; Silberstein, A. L.; Komaromi, A.; Blackburn, T.;
Ramgren, S. D.; Houk, K. N.; Snieckus, V.; Garg, N. K., J.
Am. Chem. Soc. 2011, 133, 6352. (f) Muto, K.; Yamaguchi,
J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 169. (g) Tabuchi,
S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2014, 79,
5401. (h) Ehle, A. R.; Watson, M. P. Org. Lett. 2012, 14,
1202. (i) Xu, L.; Li, B.-J.; Wu, Z.-H.; Lu, X.-Y.; Guan, B.-T.;
Wang, B.-Q.; Zhao, K.-Q.;Shi, Z.-J. Org. Lett. 2010, 12, 884.
(j) Sun, C.-L.; Wang, Y.; Zhou, X.; Wu, Z.-H.; Li, B.-J.;
Guan, B.-T.; Shi, Z.-J. Chem. Eur. J. 2010, 16, 5844. (k) Li,
B.-J.; Xu, L.; Wu, Z.-H.; Guan, B.-T.; Sun, C.-L.; Wang, B.-
Q.; Shi, Z.-J. J. Am. Chem. Soc. 2009, 131, 14656. (l) Guan,
B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem.
Soc. 2008, 130, 14468. (m) Li, B.-J.; Li, Y.-Z.; Lu, X.-Y.;
Liu, J.; Guan, B.-T.; Shi, Z.-J. Angew. Chem. Int. Ed. 2008,
47, 10124. (n) Quasdorf, K. W.; Riener, M.; Petrova, K. V.;
Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748. (o)
Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc.
2008, 130, 14422.
(10) Selected examples of C-heteroatom bonds formation via C-O
activation: (a) Zarate, C.; Martin, R. J. Am. Chem. Soc. 2014,
136, 2236. (b) Tobisu, M.; Shimasaki, T.; Chatani, N. Chem.
Lett. 2009, 38, 710. (c) Shimasaki, T.; Tobisu, M.; Chatani,
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