Journal of the American Chemical Society
Article
Shunatona, H. P.; Tkatchouk, E.; Goddard, W. A.; Toste, F. D. Angew.
Chem., Int. Ed. 2010, 49, 5519−5522. (k) Ball, L. T.; Green, M.; Lloyd-
Jones, G. C.; Russell, C. A. Org. Lett. 2010, 12, 4724−4727.
(l) Hopkinson, M. N.; Tessier, A.; Salisbury, A.; Giuffredi, G. T.;
Combettes, L. E.; Gee, A. D.; Gouverneur, V. Chem.Eur. J. 2010, 16,
4739−4743. (m) Zhang, G.; Peng, Y.; Cui, L.; Zhang, L. Angew. Chem.,
Int. Ed. 2009, 48, 3112−3115. (n) Hashmi, A. S. K.; Ramamurthi, T.
D.; Rominger, F. J. Organomet. Chem. 2009, 694, 592−597.
(o) Wegner, H. A.; Ahles, S.; Neuburger, M. Chem.Eur. J. 2008,
14, 11310−11313. (p) Hashmi, A. S. K.; Blanco, M. C.; Fischer, D.;
Bats, J. W. Eur. J. Org. Chem. 2006, 1387−1389.
(15) During optimization studies, reaction at −78 °C was observed
but conversion was very slow. To achieve a balance of selectivity and
reactivity, reactions at −50 °C were reported in ref 10.
(16) Komiya, S.; Ozaki, S. Chem. Lett. 1988, 17, 1431−1432.
(17) Guerinot, A.; Serra-Muns, A.; Bensiussan, C.; Reymond, S.;
Cossy, J. Tetrahedron 2011, 67, 5024.
(18) Unsworth, W. P.; Stevens, K.; Lamont, S. G.; Robertson, J.
Chem. Commun. 2011, 47, 7659−7661.
(19) Frisch, M. J.; et al. Gaussian 09, revision A.02; Gaussian, Inc.:
Wallingford, CT, 2009.
(20) (a) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215−
241. (b) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157−167.
(21) Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B
2009, 113, 6378−6396.
(22) For leading references, see: (a) Jagdale, A. R.; Park, J. H.; Youn,
S. W. J. Org. Chem. 2011, 76, 7204−7215. (b) Dombray, T.; Blanc, A.;
Weibel, J.; Pale, P. Org. Lett. 2010, 12, 5362−5365. (c) Lin, C.-C.;
Teng, T.-M.; Tsai, C.-C.; Liao, H.-Y.; Liu, R.-S. J. Am. Chem. Soc. 2008,
130, 16417−16423. (d) Dudnik, A. S.; Sromek, A. W.; Rubina, M.;
Kim, J. T.; Kel’in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130,
1440−1452. (e) Lin, C.-C.; Teng, T.-M.; Odedra, A.; Liu, R.-S. J. Am.
Chem. Soc. 2007, 129, 3798−3799. (f) Sromek, A. W.; Rubina, M.;
Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500−10501.
(9) (a) Mankad, N. P.; Toste, F. D. Chem. Sci. 2012, 3, 72−76.
(b) Zhang, G.; Cui, L.; Wang, Y.; Zhang, L. J. Am. Chem. Soc. 2010,
132, 1474−1475. (c) Iglesias, A.; Mun
10563−10569.
iz, K. Chem.Eur. J. 2009, 15,
(10) (a) Aponick, A.; Li, C.-Y.; Biannic, B. A. Org. Lett. 2008, 10,
669−671. (b) Aponick, A.; Biannic, B. Synthesis 2008, 20, 3356−3359.
(11) For leading references, see: (a) Wang, Z. J.; Benitez, D.;
Tkatchouk, E.; Goddard, W. A., III; Toste, F. D. J. Am. Chem. Soc.
2010, 132, 13064−13071. (b) LaLonde, R. L.; Wang, Z. J.; Mba, M.;
Lackner, A. D.; Toste, F. D. Angew. Chem., Int. Ed. 2010, 49, 598−601.
(c) Zhang, Z.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2007, 46,
283−285. (d) Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D.
Science 2007, 317, 496−499.
(23) (a) Gom
P. Dalton Trans. 2012, 41, 5461−5463. (b) Ramon
Poater, A.; Cavallo, L.; Slawin, A. M. Z.; Nolan, S. P. Chem.Eur. J.
2011, 17, 1238−1246. (c) Gaillard, S.; Slawin, A. M. Z.; Nolan, S. P.
Chem. Commun. 2010, 46, 2742−2744.
́
ez-Suar
́
ez, A.; Ramon
́
, R. S.; Slawin, A. M. Z.; Nolan, S.
, R. S.; Gaillard, S.;
́
(12) (a) Biannic, B.; Aponick, A. Eur. J. Org. Chem. 2011, 6605−
6617. (b) Aponick, A.; Li, C.-Y.; Palmes, J. A. Org. Lett. 2009, 11,
121−124. (c) Aponick, A.; Li, C.-Y.; Malinge, J.; Marques, E. F. Org.
Lett. 2009, 11, 4624−4627. (d) Aponick, A.; Biannic, B; Jong, M. R.
Chem. Commun. 2010, 46, 6849−6851. (e) Mukherjee, P.;
Widenhoefer, R. A. Angew. Chem., Int. Ed. 2012, 49, 1405−1407.
(f) Mukherjee, P.; Widenhoefer, R. A. Org. Lett. 2011, 13, 1334−1337.
(g) Mukherjee, P.; Widenhoefer, R. A. Org. Lett. 2010, 12, 1184−1187.
(h) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9533−
9537. (i) Bandini, M.; Monari, M.; Romaniello, A.; Tragni, M. Chem.−
Eur. J. 2010, 16, 14272−14277.
(13) Other metal-based catalysts have also been employed in
substitution reactions of allylic alcohols. For leading references, see:
(a) Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Org. Chem. 1997,
62, 4877−4879. (b) Yang, S.-C.; Tsai, Y.-C. Organometallics 2001, 20,
763−770. (c) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.;
Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968−10969.
(d) Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6,
4085−4088. (e) Uenishi, J.; Ohmi, M.; Ueda, A. Tetrahedron:
Asymmetry 2005, 16, 1299−1303. (f) Kawai, N.; Lagrange, J.-M.;
Ohmi, M.; Uenishi, J. J. Org. Chem. 2006, 71, 4530−4537. (g) Kawai,
N.; Lagrange, J.-M.; Uenishi, J. Eur. J. Org. Chem. 2007, 2808−2814.
(h) Uenishi, J.; Vikhe, Y. S.; Kawai, N. Chem.Asian J. 2008, 3, 473−
484. (i) Utsunomiya, M.; Miyamoto, Y.; Ipposhi, J.; Ohshima, T.;
Mashima, K. Org. Lett. 2007, 9, 3371−3374. (j) Mora, G.; Piechaczyk,
(24) Aponick, A.; Biannic, B. Org. Lett. 2011, 13, 1330−1333.
(25) For reviews, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901−
1930. (b) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48,
7383−7423.
(26) Streitwieser, A.; Jayasree, E. G.; Hasanayn, J.; Leung, S. S.-H. J.
Org. Chem. 2008, 73, 9426−9434.
(27) (a) Gimeno, M. C.; Laguna, A. Chem. Rev. 1997, 97, 511−522.
(b) Schulte, P.; Behrens, U. Chem. Commun. 1998, 1633−1634.
(c) Flores, J. A.; Dias, H. V. R. Inorg. Chem. 2008, 47, 4448−4450.
(d) Dias, H. V. R.; Fianchini, M.; Cundari, T. R.; Campana, C. F.
Angew. Chem., Int. Ed. 2008, 47, 556−559. (e) Carvajal, M. G.; Novoa,
J. J.; Alvarez, S. J. Am. Chem. Soc. 2004, 126, 1465−1477.
(f) Schwerdtfeger, P.; Hermann, H. L.; Schmidbaur, H. Inorg. Chem.
2003, 42, 1334−1342.
(28) For leading references, see: (a) Fan
Organometallics 2009, 28, 666−668. (b) Frem
́
́
-Mastral, M.; Aznar, F.
ont, P.; Marion, N.;
Nolan, S. P. J. Organomet. Chem. 2009, 694, 551−560. (c) Wu, J.;
Kroll, P.; Dias, H. V. R. Inorg. Chem. 2009, 48, 423−425. (d) Brown,
T. J.; Dickens, M. G.; Widenhoefer, R. A. Chem. Commun. 2009,
6451−6453. (e) Hooper, T. N.; Green, M.; McGrady, J. E.; Patel, J. R.;
Russell, C. A. Chem. Commun. 2009, 3877−3879. (f) Liu, L.-P.; Xu, B.;
Mashuta, M. S.; Hammond, G. B. J. Am. Chem. Soc. 2008, 130, 17642−
17643. (g) Shapiro, N. D.; Toste, F. D. Proc. Natl. Acad. Sci. U.S.A.
2008, 105, 2779−2782. (h) Lavallo, V.; Frey, G. D.; Donnadieu, B.;
Soleilhavoup, M.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5224−
O.; Houdard, R.; Mez
́
ailles, N.; Le Goff, X.-F.; Le Floch, P. Chem.
Eur. J. 2008, 14, 10047−10057. (k) Ohshima, T.; Miyamoto, Y.;
Yasuhito, J.; Nakahara, Y.; Utsunomiya, M.; Mashima, K. J. Am. Chem.
Soc. 2009, 131, 14317−14328. (l) Kabalka, G. W.; Dong, G.;
Venkataiah, B. Org. Lett. 2003, 5, 893−895. (m) Zaitsev, A. B.;
5228. (i) Furstner, A.; Alcarazo, M.; Goddard, R.; Lehmann, C. W.
̈
Angew. Chem., Int. Ed. 2008, 47, 3210−3214.
(29) For a mechanistic proposal involving amine nucleophiles, see ref
12g.
Gruber, S.; Pluss, P. A.; Pregosin, P. S.; Veiros, Worle, M. J. Am. Chem.
̈
̈
(30) For examples, see: (a) Cheong, P. H.; Morganelli, P.; Luzung,
M. R.; Houk, K. N.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 4517.
(b) Kovacs, G.; Ujaque, G.; Lledos, A. J. Am. Chem. Soc. 2008, 130,
́ ́
Soc. 2008, 130, 11604−11605. (n) van Rijn, J. A.; Lutz, M.; von
Chrzanowski, L. S.; Spek, L. A.; Bouwman, E.; Drent, E. Adv. Synth.
Catal. 2009, 351, 1637−1647. (o) Tanaka, S.; Seki, T.; Kitamura, M.
853. (c) Bo, C.; Maseras, F. Dalton Trans. 2008, 2911. (d) Paton, R.
S.; Maseras, F. Org. Lett. 2009, 11, 2237. (e) Liu, L.-P.; Malhotra, D.;
Paton, R. S.; Houk, K. N.; Hammond, G. B. Angew. Chem., Int. Ed.
2010, 49, 9132−9135.
́
Angew. Chem., Int. Ed. 2009, 48, 8948−8951. (p) Guerinot, A.; Serra-
Muns, A.; Gnamm, C.; Bensoussan, C.; Reymond, S.; Cossy, J. Org.
Lett. 2010, 12, 1808−1811. (q) Qin, H.; Yamagiwa, N.; Matsunaga, S.;
Shibasaki, M. Angew. Chem., Int. Ed. 2007, 46, 409−413. (r) Lafrance,
M.; Roggen, M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51,
3470−3473. (s) Miyata, K.; Katsuna, H.; Kawakami, S.; Kitamura, M.
Angew. Chem., Int. Ed. 2011, 50, 4649−4653. (t) Miyata, K.; Kitamura,
M. Synthesis 2012, 44, 2138−2146.
(31) (a) Kozuch, S.; Shaik, S. J. Phys. Chem. A 2008, 112, 6032−
6041. (b) Kozuch, S.; Shaik, S. Acc. Chem. Res. 2011, 44, 101−110.
(32) Brown, T. J.; Weber, D.; Gagne,
Am. Chem. Soc. 2012, 134, 9134−9137.
́
M. R.; Widenhoefer, R. A. J.
(14) Yang, C.-G.; He, C. J. Am. Chem. Soc. 2005, 127, 6966−6967.
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